- Palladium-Catalyzed Reductive Carbonylation of (Hetero) Aryl Halides and Triflates Using Cobalt Carbonyl as CO Source
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An efficient protocol for the reductive carbonylation of (hetero) aryl halides and triflates under CO gas-free conditions using Pd/Co2(CO)8 and triethylsilane has been developed. The mild reaction conditions, enhanced chemoselectivity and, easy access to heterocyclic and vinyl carboxaldehydes highlights its importance in organic synthesis.
- Dogga, Bhushanarao,Joseph, Jayan T.,Kumar, C. S. Ananda
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supporting information
p. 309 - 313
(2020/12/23)
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- Decarboxylative formylation of aryl halides with glyoxylic acid by palladium catalysis under oxygen
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A new free radical/palladium cooperative catalyzed formylation of aryl halides with glyoxylic acid as the formyl source under oxygen conditions has been developed. Various aromatic and heteroaromatic aldehydes were produced in medium to good yields.
- Cao, Hualiang,Pu, Weiwen,Zhang, Jie,Yan, Peijun,Zhang, Jun,Xu, Sheng
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supporting information
p. 1287 - 1290
(2020/08/21)
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- Synthesis and Evaluation of Indole-Based Autoinducers on Quorum Sensing in Vibrio cholerae
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Vibrio cholerae (V. cholerae) uses the autoinducer CAI-1 (cholera autoinducer 1) and several linked quorum sensing systems in order to efficiently sense its ever-changing environment and optimally coordinate population-wide gene expression. Indole has been reported as an important signal that is sensed by V. cholerae, and here, we report the synthesis and evaluation of a focused library of synthetic indole-CAI-1 derivatives as tools to probe quorum sensing (QS) in this human pathogen. Our results show interesting and diverging effects for several conjugates, as compared to CAI-1, on virulence factor production and biofilm formation.
- Holoidovsky, Lara,Meijler, Michael M.
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p. 572 - 576
(2020/04/30)
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- Nitrile Synthesis by Aerobic Oxidation of Primary Amines and in situ Generated Imines from Aldehydes and Ammonium Salt with Grubbs Catalyst
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Herein, a Grubbs-catalyzed route for the synthesis of nitriles via the aerobic oxidation of primary amines is reported. This reaction accommodates a variety of substrates, including simple primary amines, sterically hindered β,β-disubstituted amines, allylamine, benzylamines, and α-amino esters. Reaction compatibility with various functionalities is also noted, particularly with alkenes, alkynes, halogens, esters, silyl ethers, and free hydroxyl groups. The nitriles were also synthesized via the oxidation of imines generated from aldehydes and NH4OAc in situ. (Figure presented.).
- Utsumi, Tatsuki,Noda, Kenta,Kawauchi, Daichi,Ueda, Hirofumi,Tokuyama, Hidetoshi
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p. 3583 - 3588
(2020/08/05)
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- Synthesis method of 5-formylindole
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The invention discloses a synthesis method of formylindole. The synthesis method comprises the following processing steps: S1, dissolving the raw material indole in a solvent at room temperature, carrying out heating to 35-45 DEG C, and completely dissolving the raw material; and S2, slowly adding a catalyst into a mixed solvent of indole and ethyl formate, carrying out refluxing at 45-55 DEG C for 5-48 h, and performing cooling, crystallizing and filtering to obtain 5-formylindole, wherein the solvent used in the step S1 is one or more selected from the group consisting of methyl formate, ethyl formate, propyl formate and butyl formate, and the use amount of the solvent in the step S1 is 4-10 times the mass of indole. The method is mild in reaction, simple to operate, high in final product yield and good in quality.
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Paragraph 0011; 0016-0023
(2020/02/10)
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- Aromatic aldehyde synthesis method
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The invention provides an aromatic aldehyde synthesis method. Aryl halide serves as a starting material, glyoxylic acid serves as a carbonyl source, proper palladium catalysts and phosphine-containingorganic ligands are used, and aromatic aldehyde serving as a target product is prepared by heating and sealing reaction. Raw materials of the synthesis method are easily obtained, operation is simple, the product is easily separated, total reaction rate is high, process cost is low, and the yield of the target product is easily adjusted. Therefore, the aromatic aldehyde synthesis method is beneficial to large-scale industrial production of the aromatic aldehyde.
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Paragraph 0089-0094
(2019/07/04)
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- MAGNETICALLY SEPARABLE IRON-BASED HETEROGENEOUS CATALYSTS FOR DEHYDROGENATION OF ALCOHOLS AND AMINES
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The present invention discloses an iron-based nitrogen doped graphene catalyst, process for preparation thereof and use of said catalyst in oxidant-free catalytic dehydrogenation of alcohols and amines to the corresponding carbonyl compounds, amines and N-heterocylic compounds with extraction of molecular hydrogen as the only by-product.
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Page/Page column 19; 20; 21; 22
(2016/12/22)
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- MAP4K4 (HGK) Inhibitors
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The invention provides mitogen-activated protein kinase kinase kinase kinase 4 (MAP4K4) inhibitors, and pharmaceutically acceptable salts, hydrides and stereoisomers thereof. The compounds are employed in pharmaceutical compositions, and methods of making and use, including treating a person in need thereof with an effective amount of the compound or composition, and detecting a resultant diminution of tumor cell growth, cancer or metastasis.
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Paragraph 093
(2016/08/10)
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- 5-Oxo-ETE receptor antagonists
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5-Oxo-ETE is the most powerful eosinophil chemoattractant among lipid mediators. Eosinophil infiltration into the lungs of asthmatics may be responsible for the late phase of inflammatory asthma. We have designed and synthesized a 5-oxo-ETE receptor antagonist, the purpose of which is to prevent eosinophil migration to the lung during an asthma attack and thereby reduce asthma symptoms.
- Gore, Vivek,Patel, Pranav,Chang, Chih-Tsung,Sivendran, Sashikala,Kang, Namin,Ouedraogo, Yannick P.,Gravel, Sylvie,Powell, William S.,Rokach, Joshua
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p. 3725 - 3732
(2013/06/27)
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- Palladium-catalyzed nitromethylation of aryl halides: An orthogonal formylation equivalent
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An efficient cross-coupling reaction of aryl halides and nitromethane was developed with the use of parallel microscale experimentation. The arylnitromethane products are precursors for numerous useful synthetic products. An efficient method for their direct conversion to the corresponding oximes and aldehydes in a one-pot operation has been discovered. The process exploits inexpensive nitromethane as a carbonyl equivalent, providing a mild and convenient formylation method that is compatible with many functional groups.
- Walvoord, Ryan R.,Berritt, Simon,Kozlowski, Marisa C.
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supporting information; experimental part
p. 4086 - 4089
(2012/09/22)
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- Reductive carbonylation of aryl and heteroaryl iodides using Pd(acac) 2/dppm as an efficient catalyst
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Palladium catalyzed simple and efficient protocol for reductive carbonylation of aryl and heteroaryl compounds has been developed. The formylation of aryl and heteroaryl iodides takes place in the presence of Pd(acac)2/dppm catalyst at 10 bar pressure of synthetic gas to give the desired aromatic and heteroaromatic aldehydes in good to excellent yields. Easy work-up, stability of the catalyst, low catalyst loading and less reaction time are the advantages of this method.
- Singh, Abhilash S.,Bhanage, Bhalchandra M.,Nagarkar, Jayashree M.
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experimental part
p. 2383 - 2386
(2011/05/09)
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- Design of new antifungal agents: synthesis and evaluation of 1-[(1H-indol-5-ylmethyl)amino]-2-phenyl-3-(1H-1,2,4-triazol-1-yl)propan- 2-ols
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We previously reported on the design and synthesis of 1-[((hetero)aryl- or piperidinylmethyl)amino]-2-phenyl-3-(1H-1,2,4-triazol-1-yl)propan-2-ols showing various degrees of antifungal activity against Candida albicans and Aspergillus fumigatus strains. N
- Guillon, Remi,Giraud, Francis,Loge, Cedric,Le Borgne, Marc,Picot, Carine,Pagniez, Fabrice,Le Pape, Patrice
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scheme or table
p. 5833 - 5836
(2010/04/28)
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- The discovery and preparation of disubstituted novel amino-aryl-piperidine- based renin inhibitors
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Recently, trans-disubstituted oxo-aryl-piperidines have been identified as small molecule nonpeptide renin inhibitors for the modulation of hypertension. Herein, we report on the discovery and preparation of a new class of novel cis-disubstituted amino-aryl-piperidines as a mixture of enantiomers that are potent in vitro renin inhibitors and also, possess in vivo antihypertensive activity in a double transgenic mouse model.
- Cody, Wayne L.,Holsworth, Daniel D.,Powell, Noel A.,Jalaie, Mehran,Zhang, Erli,Wang, Wei,Samas, Brian,Bryant, John,Ostroski, Robert,Ryan, Michael J.,Edmunds, Jeremy J.
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- New practical synthesis of 5-formylindole
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5-Formylindole (2) was synthesized in good overall yield starting from 3-methyl-4-nitrobenzaldehyde (4) by utilization of the Batcho-Leimgruber indole synthesis.
- Fetter, Jozsef,Bertha, Ferenc,Poszavacz, Laszlo,Simig, Gyula
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p. 137 - 139
(2007/10/03)
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- Indolinone compounds as kinase inhibitors
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The invention relates to certain indolinone compounds, their method of synthesis, and a combinatorial library consisting of the indolinone compounds of the invention. The invention also relates to methods of modulating the function of protein kinases using indolinone compounds of the invention and methods of treating diseases by modulating the function of protein kinases and related signal transduction pathways.
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Page/Page column 84
(2010/11/30)
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- Glucagon antagonists/inverse agonists
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Non-peptide compounds comprising a central hydrazide motif and methods for the synthesis thereof are disclosed. The compounds act to antagonize the action of the glucagon peptide hormone.
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- Compounds as delta opioid agonists
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Compounds of the formula (I)—shown below—are described. The compounds are useful in the manufacture of a pharmaceutical composition for preventing or treating inflammatory diseases such as arthritis, psoriasis, asthma, or inflammatory bowel disease, disorders of respiratory function, gastrointestinal disorders such as functional bowel disease, functional GI disorders such as irritable bowel syndrome, functional diarrhoea, functional distension, functional pain, non-ulcerogenic dyspepsia or others associated with disorders of motility or secretion, urogenital tract disorders such as incontinence, as analgesics for treating pain including non-somatic pain, or as immunosuppressants to prevent rejection in organ transplant and skin graft.
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- Parallel synthesis of aldehydes and ketone facilitated by a new solid- phase Weinreb amide
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This paper describes a novel supported Weinreb amide resin that facilitates parallel synthesis of aldehydes and ketones on a scale useful for chemical library synthesis. This new resin makes it possible to produce custom aldehydes and ketones from a wide range of carboxylic acids, including N-BOC-amino acids. A variety of commercially unavailable aldehydes are easily synthesized in parallel and obtained in high purity via a simple filtration workup, thus facilitating parallel synthesis of lead optimization libraries that typically require custom synthesis of aldehyde intermediates for development of structure-activity relationships. To demonstrate the utility of this method, we synthesized a small library based on a supported Horner- Emmons reagent. This is the first time it has been shown that aldehydes generated via a supported Weinreb amide could be used directly as reagents in chemical library synthesis employing moisture-sensitive reactions. The analogous solution reaction is not suited for parallel synthesis because of the laborious extractive workup procedure necessary and, at times, the instability of these reactive intermediates.
- Salvino, Joseph M.,Mervic, Miljenko,Mason, Helen J.,Kiesow, Terence,Teager, David,Airey, John,Labaudiniere, Richard
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p. 1823 - 1830
(2007/10/03)
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- Propenone derivatives
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The present invention relates to propenone derivatives represented by the following formula (I): STR1 wherein R1 represents hydrogen, substituted or unsubstituted lower alkyl, substituted or unsubstituted aryl, or YR5 (wherein Y represents S or O; and R5 represents substituted or unsubstituted lower alkyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, or a substituted or unsubstituted cyclic ether residue); R2 and R3 independently represent hydrogen, lower alkyl, or substituted or unsubstituted aralkyl, or alternatively R2 and R3 are combined to form substituted or unsubstituted methylene or ethylene; R4 represents hydrogen, hydroxy, lower alkyl, substituted or unsubstituted aralkyl, lower alkoxy, substituted or unsubstituted aralkyloxy, or halogen; and X represents substituted or unsubstituted indolyl; or pharmaceutically acceptable salts thereof.
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- PROPENONE DERIVATIVES
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The present invention relates to propenone derivatives represented by the following formula (I): wherein R1represents substituted lower alkyl or YR5(wherein Y represents S or O, and R5represents substituted or unsubstitute
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- Indolyl tetrahydropyridines for treating migraine
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STR1 The present invention is concerned with compounds of formula (I), wherein n is an integer of from 0 to 3: W is a group of formula (i), (ii), or (iii), wherein R is hydrogen or C1-4 alkyl, X is --O--, --S--, --NH--, or --CH2 --, Y is oxygen or sulphur and the chiral center (*) in formula (i) or (ii) is in its (S) or (R) form or is a mixture thereof in any proportions: and Z is a group of formula (iv), (v), or (vi), wherein R1 and R2 are independently selected from hydrogen and C1-4 alkyl and R3 is hydrogen or C1-4 alkyl; and their salts, solvates and physiologically functional derivatives, with processes for their preparation, with medicaments containing them and with their use as therapeutic agents, particularly in the prophylaxis and treatment of migraine.
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- 5-heteroyl indole derivatives
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Compounds of the formula STR1 which are useful in treating migraine and other disorders, and intermediates used in the preparation of said compounds.
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- SYNTHESIS OF SOME 5-SUBSTITUTED INDOLES
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A halogen-metal exchange strategy was employed to prepare several 5-substituted indoles from 5-bromoindole.Additional derivatives were elaborated from the formyl, acetyl, thiomethyl, boronic acid and trimethylstannyl analogues thus prepared.
- Yang, Youhua,Martin, Arnold R.,Nelson, David L.,Regan, John
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p. 1169 - 1175
(2007/10/02)
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- Alpha-aminoacyl-penicillins and cephalosporins
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Antibacterially active and animal growth-regulating novel β-lactam compounds of the formula STR1 in which R1 represents an optionally substituted radical of the formula STR2 Z represents oxygen, sulphur or --N--R13, and A represents
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- The Chemistry of Indoles. XXXIII. Substituent Effect in Regioselective Metalation of 3-Indolecarbaldehyde and Syntheses of Indoles Carrying a Carbon Side Chain at the 4-, 5-, 6-, or 7-Position
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The nature of a substituent on the pyrrole ring of 3-indolecarbaldehyde plays a significant role in governing the regioselectivity of metalation.To confirm the structures of the products, various indoles carrying a carbon side chain at the 4-, 5-, 6-, or 7-position were prepared by other methods.Synthesis of 5-substituted 1-hydroxyindoles is also described.Keywords-thallation; mercuration; 4-substituted indole; 5-substituted indole; 6-substituted indole; 7-substituted indole; regioselective metalation; 3-indolecarbaldehyde; thallation-palladation; 1-hydroxyindole
- Somei, Masanori,Saida, Yoshihiro,Komura, Naoko
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p. 4116 - 4125
(2007/10/02)
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- Metal-Halogen Exchange of Bromoindoles. A Route to Substituted Indoles
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The 4-, 5-, 6-, and 7-bromoindoles, conveniently synthesized by the Batcho-Leimgruber process, serve as efficient precursors to regiochemically pure lithiated indoles.Metal-halogen exchange was most effective if potassium hydride was used first to remove the acidic indole NH, and tert-butyllithium was used then to effect metal-halogen exchange.The resulting indolyl organometallic reagents react with a variety of electrophiles to give regioisomerically pure acylated indoles.
- Moyer, Mikel P.,Shiurba, John F.,Rapoport, Henry
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p. 5106 - 5110
(2007/10/02)
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