- Selective and efficient access to ortho, meta and para ring-substituted phenylacetylene derivatives R-[C≡C-C6H4](x)-Y (Y:H, NO2, CN, I, NH2)
-
ortho, meta and para isomers of iodo and amino ring-substituted phenylacetylene as well as rod-like arylacetylene derivatives were prepared by a simple synthetic route involving three consecutive reactions: the palladium-catalysed carbon-carbon bond forma
- Lavastre, Olivier,Cabioch, Sandrine,Dixneuf, Pierre H.,Vohlidal, Jiri
-
-
Read Online
- Synthesis of Dihydroindolo[2,3-c]carbazole as Potential Telomerase Inhibitor
-
The dictyodendrins A-E were the first marine natural products that show inhibition of telomerase. A versatile and convergent route was described for the synthesis of derivatives of these pyrrolo[2,3-c]carbazole alkaloids as potential inhibitors of telomer
- Carvajal-Miranda, Yendry,Prez-Salazar, Roy,Varela, Jess A.
-
-
Read Online
- Rhenium-Catalyzed Intramolecular Carboalkoxylation and Carboamination of Alkynes for the Synthesis of C3-Substituted Benzofurans and Indoles
-
A rhenium-catalyzed carboalkoxylation and carboamination of alkyne is reported. This reaction provides an efficient route to synthesize de novo C3-substituted benzofurans and indoles under mild conditions in moderate to good yields. Mechanistic studies re
- Rong, Ming-Guang,Qin, Tian-Zhu,Zi, Weiwei
-
-
Read Online
- Metal-free cascade boron–heteroatom addition and alkylation with diazo compounds
-
Transition metal-catalyzed carbene transfer reaction is one of the most notable advances for C?C bond formation reactionsduring the past decade, which has been widely employed in the preparation of C3-substituted indoles. Here, we described an efficient e
- Lv, Jiahang,Zhao, Binlin,Han, Ying,Yuan, Yu,Shi, Zhuangzhi
-
-
Read Online
- Pyreno[2,1-b]pyrrole and bis(pyreno[2,1-b]pyrrole) as selective chemosensors of fluoride ion: A mechanistic study
-
(Chemical Equation Presented) Pyreno[2,1-b]pyrrole and its dimeric derivative display excellent selectivity and sensitivity for detection of fluoride ion, in comparison with chloride, bromide, iodide, acetate, dihydrogen phosphate, hydrogen sulfate, perch
- Lin, Chia-I.,Selvi, Srinivasan,Fang, Jim-Min,Chou, Pi-Tai,Lai, Chin-Hung,Cheng, Yi-Ming
-
-
Read Online
- One-Pot Access to Benzo[a]carbazoles via Palladium(II)-Catalyzed Hetero- and Carboannulations
-
A Pd(II)-catalyzed direct synthesis of benzo[a]carbazoles has been achieved through aminopalladation of alkynes, followed by intramolecular nucleophilic addition of the generated carbon-palladium bond to a tethered cyano/aldehyde group. Compared to literature procedures, this synthetic approach is operationally simple, uses simple substrates, and offers a fast intramolecular assembly resulting in the direct synthesis of benzo[a]carbazoles in which a wide variation of substituents at different sites is well-tolerated, leaving enough opportunity for diversification.
- Jash, Moumita,Das, Bimolendu,Chowdhury, Chinmay
-
-
Read Online
- 1,2,3-triazoles as amide bioisosteres: Discovery of a new class of potent HIV-1 Vif antagonists
-
RN-18 based viral infectivity factor (Vif), Vif antagonists reduce viral infectivity by rescuing APOBEC3G (A3G) expression and enhancing A3G-dependent Vif degradation. Replacement of amide functionality in RN-18 (IC50 = 6 μM) by isosteric heterocycles resulted in the discovery of a 1,2,3-trizole, Id (IC50 = 1.2 μM). We identified several potent HIV-1 inhibitors from a Id based library including 5ax (IC50 = 0.01 μM), 5bx (0.2 μM), 2ey (0.4 μM), 5ey (0.6 μM), and 6bx (0.2 μ M).
- Mohammed, Idrees,Kummetha, Indrasena Reddy,Singh, Gatikrushna,Sharova, Natalia,Lichinchi, Gianluigi,Dang, Jason,Stevenson, Mario,Rana, Tariq M.
-
-
Read Online
- Palladium-catalyzed coupling reaction of terminal alkynes with aryl iodides in the presence of indium tribromide and its application to a one-pot synthesis of 2-phenylindole
-
The use of a novel PdCl2(PPh3)2-InBr 3 reagent system to catalyze cross-coupling reactions of a variety of aryl iodides with several terminal alkynes is described. The corresponding functional alkyne derivatives were produced in good to excellent yields. Moreover, a catalytic amount of InBr3 effectively catalyzes the intramolecular cycloaddition of 2-phenylethynylaniline to form an indole skeleton in high yield.
- Sakai, Norio,Annaka, Kimiyoshi,Konakahara, Takeo
-
-
Read Online
- Phenylene ethynylene pentamers for organic electroluminescence
-
An isomeric family of eighteen triisopropylsilyl-capped phenylene ethynylene pentamers (molecular formula C60H62Si2) has been prepared by using fast parallel synthesis, for organic electroluminescence. Each pentamer was grown on a polymer support of propylaminomethylated polystyrene by using a series of palladium-catalysed reactions between aryl iodides and alkynes. "Tea bag" technology was used to carry out several different reactions simultaneously in the same flask. Here I present the syntheses of the materials, compare their photoluminescence both in solution and in the solid state (amorphous thin films) and describe the incorporation of the most promising pentamer into organic electroluminescence devices.
- Anderson
-
-
Read Online
- Rapid homogeneous-phase sonogashira coupling reactions using controlled microwave heating
-
A microwave-enhanced, rapid and efficient homogeneous-phase version of the Sonogashira reaction is presented. It has been applied to the coupling of aryl iodides, bromides, triflates, and aryl chloride, as well as pyridine and thiophene derivatives with t
- Erdelyi,Gogoll
-
-
Read Online
- Gold-Catalyzed Synthesis of π-Extended Carbazole-Based Systems and their Application as Organic Semiconductors
-
Herein we describe a gold-catalyzed bidirectional synthesis of N-heteropolycyclic compounds bearing carbazole moieties – namely π-extended benzodicarbazoles and π-extended indolocarbazoles. Overall, four previously unknown core structures were synthesized. This approach is convergent, modular and the gold-catalyzed key step comprises of a cascade reaction starting from stable di-azido compounds. The obtained molecules were fully characterized and their optical and electronic properties as well as their performance in organic thin-film transistors generated by vacuum deposition were studied. Charge-carrier mobilities of up to 0.3 cm2/Vs were measured. (Figure presented.).
- Hendrich, Christoph M.,Hannibal, Valentin D.,Eberle, Lukas,Hertwig, Leif E.,Zschieschang, Ute,Rominger, Frank,Rudolph, Matthias,Klauk, Hagen,K. Hashmi, A. Stephen
-
-
Read Online
- One-pot enyne metathesis/Diels-Alder/oxidation to six-membered silacycles with a multi-ring core: Discovery of novel fluorophores
-
Polycyclic compounds containing a six-membered silacycle are important. However, we have limited knowledge of the nature of these six-membered silacycles because methodologies for their synthesis remain under-developed. Here, we have developed a one-pot e
- Yoshioka, Shohei,Fujii, Yuki,Tsujino, Hirofumi,Uno, Tadayuki,Fujioka, Hiromichi,Arisawa, Mitsuhiro
-
-
Read Online
- ZnBr2-mediated synthesis of indoles in a ball mill by intramolecular hydroamination of 2-alkynylanilines
-
A method for the intermolecular hydroamination of 2-alkynylanilines in a planetary ball mill is described, which avoids the use of solvents during the reaction. Different additives were tested, whereby ZnBr2 in stoichiometric amounts showed the best performance in terms of yield and selectivity. Furthermore, the materials used for milling balls and beakers as well as the milling time and the rotation frequency were changed in order to achieve the best reaction conditions. As a result, two methods for the synthesis of 2-substituted 1H-indoles are described with their respective advantages and disadvantages. Both methods were used to convert different alkyl and aryl containing 2-ethynylanilines. This journal is the Partner Organisations 2014.
- Zille, Markus,Stolle, Achim,Wild, Andreas,Schubert, Ulrich S.
-
-
Read Online
- Palladium-catalyzed carbon-carbon coupling reactions using aryl Grignards
-
Coupling reactions using Pd(PPh3)4 were investigated with a number of electron donating and electron withdrawing substituents. High yields were obtained with both types of substituents. In competitive reactions the electron-withdrawi
- Gottardo, Christine,Aguirre, Andrea
-
-
Read Online
- Direct synthesis of polysubstituted quinoline derivatives by InBr 3-promoted dimerization of 2-ethynylaniline derivatives
-
InBr3 promotes the dimerization of 2-ethynylaniline derivatives containing an unsubstituted terminal carbon leading to the production of polysubstituted quinoline derivatives in good yield.
- Sakai, Norio,Annaka, Kimiyoshi,Konakahara, Takeo
-
-
Read Online
- Regioselective Synthesis of Substituted Carbazoles, Bicarbazoles, and Clausine C
-
Substituted carbazoles are efficiently constructed from 3-triflato-2-pyrones and alkynyl anilines. Multiple substituents are tolerated on the carbazole, and complete control of regiochemistry is observed. Complicated and sterically congested substitution patterns are produced. This strategy is also used to prepare substituted bicarbazoles and related biaryls. Finally, the method was showcased in a synthesis of the carbazole natural product clausine C.
- Points, Gary L.,Beaudry, Christopher M.
-
supporting information
p. 6882 - 6885
(2021/09/11)
-
- Optimization of 4,6-Disubstituted Pyrido[3,2-d]pyrimidines as Dual MNK/PIM Inhibitors to Inhibit Leukemia Cell Growth
-
Mitogen-activated protein kinase-interacting kinases (MNKs) and provirus integration in maloney murine leukemia virus kinases (PIMs) are downstream enzymes of cell proliferation signaling pathways associated with the resistance of tyrosine kinase inhibitors. MNKs and PIMs have complementary effects to regulate cap-dependent translation of oncoproteins. Dual inhibitors of MNKs and PIMs have not been developed. We developed a novel 4,6-disubstituted pyrido[3,2-d]pyrimidine compound 21o with selective inhibition of MNKs and PIMs. The IC50’s of 21o to inhibit MNK1 and MNK2 are 1 and 7 nM and those to inhibit PIM1, PIM2, and PIM3 are 43, 232, and 774 nM, respectively. 21o inhibits the growth of myeloid leukemia K562 and MOLM-13 cells with GI50’s of 2.1 and 1.2 μM, respectively. 21o decreases the levels ofp-eIF4E andp-4EBP1, the downstream products of MNKs and PIMs, as well as cap-dependent proteins c-myc, cyclin D1, and Mcl-1. 21o inhibits the growth of MOLM-13 cell xenografts without causing evident toxicity. 21o represents an innovative dual MNK/PIM inhibitor with a good pharmacokinetic profile.
- Han, Yu,Zhang, Huimin,Wang, Shuxiang,Li, Bo,Xing, Kun,Shi, Yuntao,Cao, Hongxue,Zhang, Jian,Tong, Tong,Zang, Jie,Guan, Lihong,Gao, Xiaoxiao,Wang, Yuetong,Liu, Dan,Huang, Min,Jing, Yongkui,Zhao, Linxiang
-
p. 13719 - 13735
(2021/10/01)
-
- Metal-Free and syn-Selective Hydrohalogenation of Alkynes through a Pseudo-Intramolecular Process
-
A new metal-free hydrohalogenation method for alkynes has been developed, which proceeds through a pseudo-intramolecular process. In this reaction, ethynylaniline serves as a substrate to quantitatively form an anilinium salt upon treatment with hydrochloric acid. The spatial proximity facilitates the efficient electrophilic addition of HCl to the ethynyl group in syn-mode, affording the corresponding chloroalkene without overaddition. This protocol was applied to HBr and HI, and the corresponding bromo- and iodoalkenes were obtained, respectively. The obtained chloroalkene was converted to tri-substituted alkenes possessing different aryl/alkynyl groups through Pd-catalyzed cross-coupling reactions.
- Asahara, Haruyasu,Mukaijo, Yusuke,Muragishi, Kengo,Iwai, Kento,Ito, Akitaka,Nishiwaki, Nagatoshi
-
p. 5747 - 5755
(2021/10/20)
-
- New indolo[1,2-c]quinazolines for single-crystal field-effect transistor: A united experimental and theoretical studies
-
Here, we account the synthesis and characterization of a series of symmetrical fused heterocyclic aromatic hydrocarbons (HAHs) with an indolo[1,2-c]quinazoline (IQ) as the core moiety. All the new HAHs IQ series were systematically investigated by using various spectroscopic methods. Furthermore, their photo-physical properties were supported by density functional theory (DFT) and time-dependent density functional theory (TDDFT) studies to support the experimental findings. The tetramethyl-substituted indolo[1,2-c]quinazoline (TMIQ) compound is shown to exhibit the shifted type of π–π stacking interactions, which render this series as a new semiconducting material. Single-crystal-based field-effect transistor devices of TMIQ exhibited efficient charge transport behavior, giving a p-channel field-effect mobility of 0.25 cm2?V?1?s?1 with an on/off ratio of 5 × 105.
- Puli, Venkat Swamy,Kilaru, Suresh,Bhongiri, Yadagiri,Marri, Sreenath Reddy,Tripathi, Anuj,Chetti, Prabhakar,Chatterjee, Anindita,Vukoti, Kiran Kumar,Pola, Someshwar
-
-
- Solvent-Dependent Cyclization of 2-Alkynylanilines and ClCF2COONa for the Divergent Assembly of N-(Quinolin-2-yl)amides and Quinolin-2(1 H)-ones
-
Herein, we present an expedient Cu-catalyzed [5 + 1] cyclization of 2-alkynylanilines and ClCF2COONa to divergent construction of N-(quinolin-2-yl)amides and quinolin-2(1H)-ones by regulating the reaction solvents. Notably, nitrile acts as a solvent and performs the Ritter reactions. ClCF2COONa is used as a C1 synthon in this transformation, which also represents the first example for utilization of ClCF2COONa as an efficient desiliconization reagent. The current protocol involves in situ generation of isocyanide, copper-activated alkyne, Ritter reaction and protonation.
- Wang, Ya,Zhou, Yao,Ma, Xingxing,Song, Qiuling
-
supporting information
p. 5599 - 5604
(2021/08/01)
-
- New Indolo[3,2-b]indole based small organic molecules for Organic Thin Film Transistors (OTFTs): A combined experimental and DFT Study
-
Synthesis of new indolo[3,2-b]indoles (5a- 5j) in presence of Ag-doped ZnO and (Diacetoxyiodo) benzene system under visible-light have been reported. All the new fused linear heterocyclic indolo[3,2-b]indole systems (5a- 5j) thoroughly characterized by spectroscopic methods like mass, UV-visible, NMR and C, H, N elemental analysis. Further, their photophysical properties were carried out by combined experimental and theoretical studies. Thermogravimetric studies are carried out to confirm the thermal stability of molecules. The frontier molecular orbitals of molecules are characterized with the help of cyclic voltammetry. Additionally, the compounds of series 5 were used for the fabrication of organic thin-film transistors, which indicated the hole mobilities in the range of 0.11 – 0.85 cm2/Vs and with on/off ratio 105 on ODTS-SiO2 substrate at 50 °C and are also supported by DFT studies.
- Puli, Venkat Swamy,Subburu, Mahesh,Bhongiri, Yadagiri,Tripathi, Anuj,Prasad,Chatterjee, Anindita,Pola, Someshwar,Chetti, Prabhakar
-
-
- Copper-catalyzed (4+1) and (3+2) cyclizations of iodonium ylides with alkynes
-
The copper(ii)-catalyzed (4+1) cyclizations and copper(i)-catalyzed (3+2) cycloadditions of iodonium ylides and alkynes were successfully developed by employing efficient and safe iodonium ylides instead of traditional diazo compounds. Highly functionaliz
- Liang, Hao,He, Xiaobo,Zhang, Yaqi,Chen, Bin,Ouyang, Jia-Sheng,Li, Yongsu,Pan, Bendu,Subba Reddy, Chitreddy V.,Chan, Wesley Ting Kwok,Qiu, Liqin
-
supporting information
p. 11429 - 11432
(2020/10/12)
-
- 4, 6-disubstituted pyridine [3, 2-d] pyrimidine compound as well as preparation and application thereof
-
The invention belongs to the technical field of medicines. The invention relates to the field of pharmaceutical chemistry, in particular to a 4, 6-disubstituted pyridine [3, 2-d] pyrimidine compound and pharmaceutically acceptable salt thereof, a preparation method of the compound, a pharmaceutical composition taking the compound as an active ingredient, and application of the compound in preparation of an MNK inhibitor and drugs for treating and/or preventing various cancers and/or metabolic diseases. The present invention relates to compounds represented by formulas I, II, III or IV, and pharmaceutically acceptable salts, hydrates, solvates and metabolites thereof, wherein the variables are described in the claims and the description.
- -
-
Paragraph 0100; 0116-118
(2020/04/02)
-
- Oxidative Approach Enables Efficient Access to Cyclic Azobenzenes
-
Azobenzenes are versatile photoswitches that have found widespread use in a variety of fields, ranging from photopharmacology to the material sciences. In addition to regular azobenzenes, the cyclic diazocines have recently emerged. Although diazocines have fascinating conformational and photophysical properties, their use has been limited by their synthetic accessibility. Herein, we present a general, high-yielding protocol that relies on the oxidative cyclization of dianilines. In combination with a modular substrate synthesis, it allows for rapid access to diversely functionalized diazocines on gram scales. Our work systematically explores substituent effects on the photoisomerization and thermal relaxation of diazocines. It will enable their incorporation into a wide variety of functional molecules, unlocking the full potential of these emerging photoswitches. The method can be applied to the synthesis of a new cyclic azobenzene with a nine-membered central ring and distinct properties.
- Maier, Martin S.,Hüll, Katharina,Reynders, Martin,Matsuura, Bryan S.,Leippe, Philipp,Ko, Tongil,Sch?ffer, Lukas,Trauner, Dirk
-
supporting information
p. 17295 - 17304
(2019/11/03)
-
- Design, synthesis, and structure-activity relationship of 7-propanamide benzoxaboroles as potent anticancer agents
-
Benzoxaboroles, as a novel class of bioactive molecules with unique physicochemical properties, have been shown to possess excellent antimicrobial activities with tavaborole approved in 2014 as an antifungal drug. Although urgently needed, the investigation of benzoxaboroles as anticancer agents has been lacking so far. In this study, we report the design, synthesis, and anticancer structure-activity relationship of a series of 7-propanamide benzoxaboroles. Compounds 103 and 115 showed potent activity against ovarian cancer cells with IC50 values of 33 and 21 nM, respectively. Apoptosis was induced by these compounds and colony formation was effectively inhibited. Furthermore, they also showed excellent efficacy in ovarian tumor xenograft mouse model.
- Zhang, Jiong,Zhang, Jinyi,Hao, Guiyun,Xin, Weixiang,Yang, Fei,Zhu, Mingyan,Zhou, Huchen
-
p. 6765 - 6784
(2019/08/20)
-
- Copper-Catalyzed Tandem Cross-Coupling/[2 + 2] Cycloaddition of 1,6-Allenynes with Diazo Compounds to 3-Azabicyclo[5.2.0] Ring Systems
-
An unprecedented copper-catalyzed tandem cross-coupling/[2 + 2] cycloaddition of 1,6-allenynes with diazo compounds was reported, chemo- and regioselectively providing 3-azabicyclo[5.2.0] frameworks in moderate to excellent yields under mild reaction conditions. Moreover, the products readily convert to highly functionalized quinolines via oxidative radical rearrangement.
- He, Min,Chen, Nuan,Zhou, Ting,Li, Qing,Li, Hongguang,Lang, Ming,Wang, Jian,Peng, Shiyong
-
supporting information
p. 9559 - 9563
(2019/11/21)
-
- Gold-catalyzed tandem reaction of 2-alkynylanilines followed by 1,6-conjugate addition to: P -quinone methides: Efficient access to unsymmetrical diarylindolylmethanes
-
A simple, mild, efficient and chemoselective catalytic method for the straightforward synthesis of an interesting class of 2-aryl/alkyl-substituted-3-diaryl indolyl methanes in high yield is reported. This atom-efficient method proceeds via a gold-catalyzed one-pot sequential intramolecular hydroamination (C-N bond formation) of 2-alkynylanilines followed by a 1,6-conjugate addition to p-quinonemethides. The p-quinonemethides, which contain aldehyde functional groups, preferentially participate in 1,6-conjugate addition, while the aldehyde functional group remains unreactive.
- Jillella, Raveendra,Oh, Dong Hwan,Oh, Chang Ho
-
supporting information
p. 16886 - 16890
(2018/10/23)
-
- Boron Trichloride-Mediated Synthesis of Indoles via the Aminoboration of Alkynes
-
We describe an efficient catalyst- and metal-free aminoboration of alkynes to 3-borylated indoles using one of the least expensive boron sources, BCl3. The major dichloro(indolyl)borane products can be used for the in situ construction of usefu
- Lv, Jiahang,Zhao, Binlin,Liu, Li,Han, Ying,Yuan, Yu,Shi, Zhuangzhi
-
supporting information
p. 4054 - 4059
(2018/09/25)
-
- PtCl4-catalyzed cyclization of N-acetyl-2-alkynylanilines: A mild and efficient synthesis of N-acetyl-2-substituted indoles
-
An efficient synthesis of N-acetyl-2-substituted indole derivatives via direct intramolecular hydroamination of N-acetyl-2-alkynylaniline derivatives was developed. The reaction could be applied to a wide range of substrates employing only 1–2 mol% of PtCl4 as the catalyst to furnish the desired indole products in moderate to excellent yields. The current protocol is efficient, reliable and scalable, and could serve as an important tool for convenient and rapid access to this important class of N-heterocyclic skeleton from readily available substrates.
- Chaisan, Nattawadee,Kaewsri, Wilailak,Thongsornkleeb, Charnsak,Tummatorn, Jumreang,Ruchirawat, Somsak
-
supporting information
p. 675 - 680
(2018/01/18)
-
- Synthesis of 2-(Trifluoromethyl)indoles via Domino Trifluoromethylation/Cyclization of 2-Alkynylanilines
-
A new method for the synthesis of 2-(trifluoromethyl)indoles using easily accessible 2-alkynylanilines and a well-established fluoroform-derived CuCF3 reagent is described. This method utilizes a domino trifluoromethylation/cyclization strategy
- Ye, Yibin,Cheung, Kelvin Pak Shing,He, Lisi,Tsui, Gavin Chit
-
supporting information
p. 1676 - 1679
(2018/03/23)
-
- Total Synthesis of Dictyodendrins by the Gold-Catalyzed Cascade Cyclization of Conjugated Diynes with Pyrroles
-
In total and formal syntheses of dictyodendrins B, C, E, and F, the key step involved the direct construction of the pyrrolo[2,3-c]carbazole core by the gold-catalyzed annulation of a conjugated diyne with a pyrrole to form three bonds and two aromatic rings. The subsequent introduction of substituents at the C1 (Suzuki–Miyaura coupling), C2 (addition to an aldehyde), N3 (alkylation), and C5 positions (Ullman coupling) provided divergent access to dictyodendrins.
- Matsuoka, Junpei,Matsuda, Yuka,Kawada, Yuiki,Oishi, Shinya,Ohno, Hiroaki
-
supporting information
p. 7444 - 7448
(2017/06/13)
-
- Indole synthesis via cyclative formation of 2,3-dizincioindoles and regioselective electrophilic trapping
-
Upon zincation of two acidic protons attached to the nitrogen and the sp-carbon atoms, a N-protected 2-ethynylaniline cyclizes to a 2,3-dizincioindole at 120 °C. Driven by the energy gain due to formation of two C-Zn bonds, this reaction occurs smoothly without side reactions, although this transformation is intrinsically endothermie in its bare anionic form. The resulting dizinc intermediate can be functionalized with one or two different electrophiles either inter- or intramolecularly on either C2 or C3 selectively, depending on the choice of catalyst and the electrophiles. This conversion of 2-ethynylaniline to 2,3-dimetalloindole can be applied to an expeditious synthesis of indenoindolone and benzodipyrrole derivatives, which are compounds of interest for medicinal chemistry and materials science, respectively.
- Ilies, Laurean,Isomura, Mayuko,Yamauchi, Shin-Ichi,Nakamura, Tomoya,Nakamura, Eiichi
-
supporting information
p. 23 - 26
(2017/05/16)
-
- ALKYNYL PHOSPHINE GOLD COMPLEXES FOR TREATING BACTERIAL INFECTIONS
-
A compound of formula (I) for use in the prevention or treatment of a bacterial infection.
- -
-
Page/Page column 99
(2017/08/01)
-
- Ruthenium-Catalyzed 1,6-Aromatic Enamide-Silylalkyne Cycloisomerization: Approach to 2,3-Disubstituted Indoles
-
Cycloisomerization is an atom economic procedure that converts dienes and enynes into cyclic molecules. To date, cycloisomerization between enamides and silylalkynes has not been explored. We found that N-acyl-N-vinyl-2-silylalkynylaniline derivatives und
- Takamoto, Kohei,Ohno, Shohei,Hyogo, Norimichi,Fujioka, Hiromichi,Arisawa, Mitsuhiro
-
p. 8733 - 8742
(2017/08/23)
-
- BROAD SPECTRUM ANTIVIRAL COMPOUNDS AND USES THEREOF
-
Disclosed herein, inter alia, are agents having antiviral activity and methods of use thereof.
- -
-
Paragraph 0453
(2017/03/21)
-
- Indole [3,2-c] quinoline compound or its pharmaceutically acceptable salts and its preparation method and application
-
The invention discloses indole[3,2-c]quinoline compounds represented by formula I or pharmaceutically acceptable salts thereof, and a preparation method and an application thereof, and belongs to the technical field of the pharmaceutical chemistry. The in
- -
-
Paragraph 0033
(2016/10/10)
-
- CuI-Catalyzed intramolecular aminocyanation of terminal alkynes in N-(2-ethynylphenyl)-N-sulfonylcyanamides via Cu-vinylidene intermediates
-
CuI-Catalyzed intramolecular aminocyanation of terminal alkynes in N-(2-ethynylphenyl)-N-sulfonylcyanamides was initiated by the formation of Cu-acetylide to trigger N-CN bond cleavage of the N-sulfonylcyanamide moiety followed by CN migration to form a β-cyano Cu-vinylidene intermediate. Subsequently, the indole ring closure furnished the corresponding 1-sulfonyl-3-cyanoindoles.
- Liao, Zhen-Yuan,Liao, Pen-Yuan,Chien, Tun-Cheng
-
supporting information
p. 14404 - 14407
(2016/12/23)
-
- Catalytic Enantioselective Synthesis of Amino Skipped Diynes
-
The Cu-catalyzed synthesis of nonracemic 3-amino skipped diynes via an enantiodetermining C-C bond formation is described using StackPhos as ligand. Despite challenging issues of reactivity and stereoselectivity inherent to these chiral skipped diynes, the reaction tolerates an extremely broad substrate scope with respect to all components and provides the title compounds in excellent enantiomeric excess. The alkyne moieties are demonstrated here to be useful synthetic handles, and 3-amino skipped diynes are convenient building blocks for enantioselective synthesis.
- Paioti, Paulo H. S.,Abboud, Khalil A.,Aponick, Aaron
-
supporting information
p. 2150 - 2153
(2016/03/05)
-
- Stereoselective Synthesis of Methylene Oxindoles via Palladium(II)-Catalyzed Intramolecular Cross-Coupling of Carbamoyl Chlorides
-
We report a highly robust, general and stereoselective method for the synthesis of 3-(chloromethylene)oxindoles from alkyne-tethered carbamoyl chlorides using PdCl2(PhCN)2 as the catalyst. The transformation involves a stereo- and regioselective chloropalladation of an internal alkyne to generate a nucleophilic vinyl PdII species, which then undergoes an intramolecular cross-coupling with a carbamoyl chloride. The reaction proceeds under mild conditions, is insensitive to the presence of moisture and air, and is readily scalable. The products obtained from this reaction are formed with >95:5 Z:E selectivity in nearly all cases and can be used to access biologically relevant oxindole cores. Through combined experimental and computational studies, we provide insight into stereo- and regioselectivity of the chloropalladation step, as well as the mechanism for the C-C bond forming process. Calculations provide support for a mechanism involving oxidative addition into the carbamoyl chloride bond to generate a high valent PdIV species, which then undergoes facile C-C reductive elimination to form the final product. Overall, the transformation constitutes a formal PdII-catalyzed intramolecular alkyne chlorocarbamoylation reaction.
- Le, Christine M.,Sperger, Theresa,Fu, Rui,Hou, Xiao,Lim, Yong Hwan,Schoenebeck, Franziska,Lautens, Mark
-
supporting information
p. 14441 - 14448
(2016/11/13)
-
- Rhodium-Catalyzed Cycloisomerization of 2-Silylethynyl Phenols and Anilines via 1,2-Silicon Migration
-
It has been established that a cationic rhodium(I)/BINAP complex catalyzes the cycloisomerization of 2-silylethynylphenols, leading to 3-silylbenzofurans, via 1,2-silicon migration. Similarly, the cycloisomerization of 2-silylethynylanilines, leading to 3-silylindoles, via 1,2-silicon migration was catalyzed by a cationic rhodium(I)/H8-BINAP complex.
- Kanno, Hiroshi,Nakamura, Kyosuke,Noguchi, Keiichi,Shibata, Yu,Tanaka, Ken
-
supporting information
p. 1654 - 1657
(2016/04/26)
-
- Pyrimidine or pyridine pyridine ketone compound and its preparation method and application (by machine translation)
-
The invention discloses a kind of type I of the pyrimidine or pyridine pyridine ketone compound and its preparation and application, which belongs to the technical field of pharmaceutical preparation. The compounds have high-efficient and selectively inhibit the cell cycle dependent kinases (Cdks) CDK4 and CDK6 active, and then by inhibiting CDK4/CDK6 prevent tumor cell division. Therefore, the compounds of this invention can be used for CDK4 and CDK6 the involved in cell cycle control disorders result in various diseases, especially suitable for the treatment of malignant tumors. (by machine translation)
- -
-
Paragraph 0292
(2016/10/09)
-
- Fluoroform-Derived CuCF3 for Trifluoromethylation of Terminal and TMS-Protected Alkynes
-
An efficient trifluoromethylation reaction of alkynes using a fluoroform-derived CuCF3 reagent is described. The CF3 source is the inexpensive industrial waste fluoroform (CF3H). The air-stable CuCF3 reagent can be prepared in large quantities and is convenient to use. Synthetically useful trifluoromethylated alkynes containing a wide range of functional groups were successfully synthesized under mild conditions. Both terminal and TMS-protected alkynes gave the products in one step. The beneficial effect of a diamine ligand tetramethylethylenediamine (TMEDA) with the fluoroform-derived CuCF3 reagent was also demonstrated.
- He, Lisi,Tsui, Gavin Chit
-
supporting information
p. 2800 - 2803
(2016/07/06)
-
- Revisiting the Gold-Catalyzed Dimerization of 2-Ethynylanilines: A Room-Temperature and Silver-Free Protocol for the Synthesis of Multifunctional Quinolines
-
A room temperature and silver-free protocol for the formation of quinolines from 2-ethynylanilines through a dimerization event was achieved using a dinuclear gold catalyst, Au2(BIPHEP)(NTf2)2. The reaction is inherently modular, allowing for the incorporation of peripheral substituents at any site of the quinoline product. The reaction is readily applied to other heterocyles also as exemplified by the preparation of naphthyridines. Competition reactions to determine the reactivity of dissimilar alkynes demonstrated that the product ratio of dimerization vs intermolecular addition is rather dependent on the electronic nature of aryl substituent on the alkynes. However, control experiments with substrates possessing internal alkynes resulted in cycloisomerization instead of expected dimerization, which is indicative of possible steric influence of the alkyne terminus in the reaction outcome.
- Praveen, Chandrasekar,Perumal
-
p. 855 - 864
(2016/03/15)
-
- Hybrid Diphenylalkyne-Dipeptide Oligomers Induce Multistrand β-Sheet Formation
-
Functionalized diphenylalkynes provide a template for the presentation of protein-like surfaces composed of multistrand β-sheets. The conformational properties of three-, four-, and seven-stranded systems have been investigated in the solid- and solution-state. This class of molecule may be suitable for the mediation of therapeutically relevant protein-protein interactions. β-Sheets: Functionalized diphenylalkynes provide a template for the presentation of protein-like surfaces composed of multi-strand β-sheets. The conformational properties of three-, four-, and seven-stranded systems have been investigated in the solid- and solution-state. This class of molecule may be suitable for the mediation of therapeutically relevant protein-protein interactions.
- Ross, Jonathan E.,Knipe, Peter C.,Thompson, Sam,Hamilton, Andrew D.
-
supporting information
p. 13518 - 13521
(2015/09/22)
-
- Aminoboration: Addition of B-N ? Bonds across C-C ?€ Bonds
-
This communication demonstrates the first catalytic aminoboration of C-C π bonds by B-N δ bonds and its application to the synthesis of 3-borylated indoles. The regiochemistry and broad functional group compatibility of this addition reaction enable substitution patterns that are incompatible with major competing technologies. This aminoboration reaction effects the formation of C-B and C-N bonds in a single step from aminoboronic esters, which are simple starting materials available on the gram scale. This reaction generates synthetically valuable N-heterocyclic organoboron compounds as potential building blocks for drug discovery. The working mechanistic hypothesis involves a bifunctional Lewis acid/base catalysis strategy involving the combination of a carbophilic gold cation and a trifluoroacetate anion that activate the C-C π bond and the B-N δ bond simultaneously.
- Chong, Eugene,Blum, Suzanne A.
-
supporting information
p. 10144 - 10147
(2015/09/01)
-
- Synthesis of 7-alkylidene-7,12-dihydroindolo[3,2-d]benzazepine-6-(5H)-ones (7-alkylidene-paullones) by N-cyclization-oxidative Heck cascade and characterization as sirtuin modulators
-
An extension of our reported protocol to benzofused heterocyclic derivatives (benzofurans, indoles, isochromeneimines), involving a palladium-induced cascade of N-cyclization and oxidative Heck reactions of o-alkynylanilines, has allowed the preparation o
- Denis,Franci,Altucci,Aurrecoechea,De Lera,lvarez
-
supporting information
p. 2800 - 2810
(2015/04/21)
-
- Unusual 1,2-aryl migration in Pd(II)-catalyzed aza-Wacker-type cyclization of 2-alkenylanilines
-
Inspired by the Hegedus aza-Wacker indole synthesis, we were intrigued with the fate of the aminopalladation intermediate if syn β-hydrogen is made inaccessible or unavailable. In contrast to our previously reported β-carbon elimination, cyclization of a
- Youn, So Won,Lee, So Ra
-
supporting information
p. 4652 - 4656
(2015/04/27)
-
- Reactivity switch enabled by counterion: Highly chemoselective dimerization and hydration of terminal alkynes
-
A counterion-controlled reactivity tuning in Pd-catalyzed highly chemoselective and regioselective dimerization and hydration of terminal alkynes is reported. The use of acetate as counterion favors the formation of an alkenyl alkynyl palladium intermediate which forms hitherto less reported 1,3-diaryl-substituted conjugated enynes after reductive elimination. Using chloride, which is a better leaving group, leads to anion exchange on the alkenylpalladium intermediate with hydroxide which after reductive elimination and tautomerization delivered the hydration products.
- Xu, Caixia,Du, Weiyuan,Zeng, Yi,Dai, Bin,Guo, Hao
-
supporting information
p. 948 - 951
(2014/03/21)
-
- Concise syntheses of meridianins and meriolins using a catalytic domino amino-palladation reaction
-
A synthesis of natural and synthetic members of the meridianin family of kinase inhibitory natural products has been developed. The sequence utilizes a variation of the Cacchi palladium-catalyzed domino reaction to efficiently construct the heterocyclic f
- Walker, Scott R.,Czyz, Milena L.,Morris, Jonathan C.
-
supporting information
p. 708 - 711
(2014/03/21)
-
- Copper-catalyzed annulation of α-substituted diazoacetates with 2-ethynylanilines: The direct synthesis of C2-functionalized indoles
-
Copper-catalyzed direct annulation of α-substituted diazoacetates with 2-ethynylanilines leading to C2-functionalized indoles was achieved under mild reaction conditions. The C2-(carboxylate methyl) substituted indoles were obtained in moderate to high yi
- Liu, Gang,Xu, Guangyang,Li, Jian,Ding, Dong,Sun, Jiangtao
-
supporting information
p. 1387 - 1390
(2014/03/21)
-
- [Cp?IrCl2]2-catalysed cyclization of 2-alkynylanilines into indoles
-
[Cp?IrCl2]2 catalyses the cyclization of 2-alkynylanilines into indoles. A wide variety of substrates is tolerated. A reaction pathway involving intramolecular hydroamination is proposed.
- Kumaran, Elumalai,Leong, Weng Kee
-
supporting information
p. 5495 - 5498
(2014/12/11)
-
- Metal-free C-H amination for indole synthesis
-
An effective metal-free C-H amination of N-Ts-2-alkenylanilines by using DDQ as an oxidant has been developed to afford a diverse range of substituted indoles. This protocol is operationally simple and robust, obviates the need of expensive transition-metal catalysts, and offers a broad substrate scope. A mechanism involving a radical cation generated by SET and a migratorial process via a phenonium ion intermediate is proposed.
- Jang, Young Ho,Youn, So Won
-
supporting information
p. 3720 - 3723
(2014/08/05)
-
- Palladium nanoparticles supported on natural nanozeolite clinoptilolite as a catalyst for ligand and copper-free C-C and C-O cross coupling reactions in aqueous medium
-
In this article, Pd0-nanoparticles supported on natural nanozeolite clinoptilolite (CP) were successfully synthesized, and the catalytic activity of the nanocatalyst was investigated in C-C and C-O coupling reactions, namely the Sonogashira and Ullmann condensation reactions in an aqueous medium. The nanocatalyst was characterized by various techniques such as powder-XRD, BET, SEM, TEM, HRTEM, TEM-EDS, ICP-OES and XPS. From an electron microscopy (SEM) study it can be inferred that the particles are mostly spherical or of ellipsoidal shape and have diameters ranging from 25 to 80 nm. A HRTEM study reveals that Pd0-nanoparticles supported on nanozeolite CP have an average diameter of ~10 nm. The supported palladium nanoparticles showed excellent catalytic activity in the synthesis of aryl alkynes and diaryl ethers in high yields. In addition, the nanocatalyst could be recycled and reused several times without significant loss of catalytic activity.
- Baghbanian, Seyed Meysam,Yadollahy, Horieh,Tajbakhsh, Mahmood,Farhang, Maryam,Biparva, Pourya
-
p. 62532 - 62543
(2015/02/19)
-
- Silver-catalyzed incorporation of carbon dioxide into o-alkynylaniline derivatives
-
Benzoxazine-2-one derivatives are important heterocycle structures because of their various pharmaceutical activities, though their synthetic methods had been limited. In some cases, toxic reagents, such as phosgene or carbon monoxide, are required. It was found that a silver catalyst successfully promoted the incorporation of CO2 into o-alkynylanilines to afford the corresponding benzoxazine-2-ones bearing Z exo-olefin via 6-exo-dig cyclization at the activated C-C triple bond.
- Ishida, Tomonobu,Kikuchi, Satoshi,Tsubo, Tatsuyuki,Yamada, Tohru
-
supporting information
p. 848 - 851
(2013/03/28)
-
- Protonated DBU as catalyst for cascade addition-cyclization of 2-alkynylaniline and carbon disulfide
-
Protonated 1,8-diazabicyclo[5,4,0]undec-7-ene as catalyst for cascade addition/cyclization of 2-alkynylaniline and carbon disulfide has been described. This process provides a convenient route for synthesis of a variety of benzo[d][1,3]thiazine-2(4H)-thio
- Zhao, Peng,Liao, Qian,Gao, Hongxin,Xi, Chanjuan
-
supporting information
p. 2357 - 2361
(2013/06/26)
-
- Synthesis of fluorine-containing multisubstituted phenanthridines by rhodium-catalyzed alkyne [2+2+2] cycloaddition and tandem sp2 C-H difluoromethylenation
-
A highly efficient method for the synthesis of fluorine-containing multisubstituted phenanthridines through Rh-catalyzed alkyne [2+2+2] cycloaddition reactions has been developed. This method exhibits excellent functional-group compatibility. When a bromodifluoromethyl group, rather than a trifluoromethyl group, was employed in the cycloaddition reaction, more-complicated polycyclic compounds were obtained through tandem Rh-catalyzed cycloaddition/C-H difluoromethylenation. This route provides convenient access to fluorine-containing polycyclic compounds. [2+2+2] Little boys: Fluorine-containing multisubstituted phenanthridines have been synthesized through Rh-catalyzed alkyne [2+2+2] cycloaddition reactions (see scheme; FG=functional group). Polycyclic compounds were also obtained through Rh-catalyzed C-H difluoromethylenation. Copyright
- Li, Yajun,Zhu, Jiangtao,Zhang, Lisi,Wu, Yongming,Gong, Yuefa
-
supporting information
p. 8294 - 8299
(2013/07/27)
-
- Rhodium-catalyzed chemo- and regioselective cross-dimerization of two terminal alkynes
-
Cross-dimerization of terminal arylacetylenes and terminal propargylic alcohols/amides has been achieved in the presence of a rhodium catalyst. This method features high chemo- and regioselectivities rendering convenient and atom economical access to functionalized enynes.
- Xu, Hua-Dong,Zhang, Ren-Wei,Li, Xiaoxun,Huang, Suyu,Tang, Weiping,Hu, Wen-Hao
-
supporting information
p. 840 - 843
(2013/03/29)
-