- One-pot approach to chiral chromenes via enantioselective organocatalytic domino oxa-Michael-aldol reaction
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A highly enantioselective (S)-diphenylpyrrolinol triethylsilyl ether promoted tandem oxa-Michael-aldol reaction of α,β-unsaturated aldehydes with salicylaldehydes has been developed; the method affords one-pot access to chiral and synthetically useful chr
- Li, Hao,Wang, Jian,E-Nunu, Timiyin,Zu, Liansuo,Jiang, Wei,Wei, Shaohua,Wang, Wei
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- Organocatalytic synthesis of chiral benzopyrans
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Benzopyrans, or chromenes, are widespread in nature and are considered to be a privileged scaffold in medicinal chemistry. Herein, we report the first organocatalyzed asymmetric synthesis of chiral benzopyrans. The benzopyran unit is constructed through a
- Govender, Thavendran,Hojabri, Leila,Moghaddam, Firouz Matloubi,Arvidsson, Per I.
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- Catalytic enantioselective domino oxa-michael/aldol condensations: Asymmetric synthesis of benzopyran derivatives
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The first direct organocatalytic asymmetric domino oxa-Michael/aldol condensation reaction is presented. The unprecedentedly simple, chiral, pyrrolidine-catalyzed asymmetric domino reactions between salicylic aldehyde derivatives and α,β-unsaturated aldeh
- Sunden, Henrik,Ibrahem, Ismail,Zhao, Gui-Ling,Eriksson, Lars,Cordova, Armando
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- Asymmetric Synthesis of Dihydropyranones with Three Contiguous Stereocenters by an NHC-Catalyzed Kinetic Resolution
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An oxidative NHC-catalyzed kinetic resolution (KR) of racemic mixtures is presented. The developed reaction furnishes tricyclic dihydropyranones with three contiguous stereocenters in excellent dia- and enantioselectivity, with good-to-moderate yields. Mechanistic studies indicate that the rate-determining step of the reaction is the formation of the Breslow intermediate, while the selectivity determining step occurs later in the mechanism. The presented methodology enables rapid synthesis of complex structures in a single step.
- Axelsson, Anton,Westerlund, Mathias,Zacharias, Savannah C.,Runemark, August,Haukka, Matti,Sundén, Henrik
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supporting information
p. 3657 - 3661
(2021/07/22)
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- A novel pyrazoline-based fluorescent probe for Cu2+ in aqueous solution and imaging in live cell
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In this study, a new pyrazoline derivate (1-acetyl-3- (2-hydroxy-1-naphthyl)-5-(2-phenyl-2H-chromene)-2-pyrazoline, N) is described as fluorescent probe for fluorometric detection of Cu2+. This fluorescence of probe has a high selectivity only toward Cu2+ ion in the other metal ions. It is remarkably observed that the fluorescence intensity of N decreased in the presence of Cu2+ ions with a strong capability to resist perturbations. The Limit of detection (LOD) value is calculated as 8.85 × 10?7 M for Cu2+ while the complexation constant is calculated as 3.14 × 105 M?2 via fluorescence measurements. The interaction between of N and Cu2+ is reversible after adding PPi. The optimized calculation of the probe for Cu2+ is confirmed by TD-DFT calculations. N-Cu2+ is successfully applied in the intracellular imaging in living PK-21cells that will have a great chance for wide application.
- Zhang, Ying-peng,Zhao, Yu-chen,Xue, Qing-hua,Yang, Yun-shang,Guo, Hui-Chen,Xue, Ji-Jun
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- Design, one-pot synthesis, molecular docking study, and antibacterial evaluation of novel 2H-chromene based imidazo[1,2-a]pyridine derivatives as potent peptide deformylase inhibitors
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An efficient, environmentally friendly, one-pot three-component synthesis of a series of 2H-chromene-based imidazo[1,2-a]pyridines had been designed and were synthesized. This protocol was developed by the reaction of substituted 2H-chromene aldehydes and
- Jena, Subhrakant,Mishra, Nilima Priyadarsini,Mohapatra, Seetaram,Nayak, Sabita,Padhy, Rabindra Nath,Raiguru, Bishnu Prasad,Sahoo, Chita Ranjan
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- Enantioselective organocatalytic synthesis of the chiral chromenes by domino oxa-Michael-aldol reaction
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The proline based chiral organocatalyst has been found to be an efficient catalyst for the facile synthesis of substituted 2-aryl-2H-chromenes-3-carbaldehyde. We envisioned that the iminium interaction between chiral amino catalysts and α,β-unsaturated ca
- Pendalwar, Shrikant S.,Chakrawar, Avinash V.,Bhusare, Sudhakar R.
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p. 942 - 944
(2017/10/23)
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- Design and synthesis of (Z/E)-2-phenyl/H-3-styryl-2H-chromene derivatives as antimicrotubule agents
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Abstract: Two new series of compounds (Z?/?E)-2-phenyl/H-3-Styryl-2H-Chromenes 9(a-r) and 10(a-s) were synthesized and evaluated in vitro cytotoxic activities against four cancer cell lines. One compound, (Z)-8-ethoxy-3-(4-methoxystyryl)-2-phenyl-2H-chrom
- Panda,Nayak,Bhakta,Mohapatra,Murthy
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- Diastereoselective synthesis of novel spiro indanone fused pyrano[3,2-: c] chromene derivatives following hetero-Diels-Alder reaction and in vitro anticancer studies
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The development of concise methods for the synthesis of small functionalised spirocyclic molecules is important in the search of new bioactive molecules. To contribute this, here we represent a diastereoselective oxa-hetero-Diels-Alder reaction for the synthesis of novel spiro indanone fused pyrano[3,2-c]chromene derivatives and studied their in vitro anticancer activities. Using previously less explored cyclic ketone i.e. indane-1,3-dione and 3-vinyl-2H-chromene derivatives, we obtained novel spiro-heterocyclic frameworks at the interphase between "drug-like" molecules and natural products. Various spiro indanone fused pyrano[3,2-c]chromene derivatives were synthesized regiospecifically bearing a quaternary stereocenter in high yields (up to 85%) with excellent diastereoselectivity in toluene using 4 ? MS as additive under reflux condition at 120 °C. In vitro cytotoxic studies of these compounds against MCF-7 (breast cancer), HCT-116 (colon cancer), H-357 (oral cancer), MD-MB-231(Breast cancer) cell lines were evaluated by MTT {3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide} assay in vitro. The screening results revealed that many of the compounds are showing moderate to high levels of anticancer activities against the tested cancer cell lines and some displayed potent inhibitory activities in comparison to the commercial anticancer drug 5-fluorouracil (5-FU). Among the series, compound 3′c showed most potent cytotoxicity (15.0-27.5 μM) in three cancer cell lines (MCF-7, HCT-116 and MD-MB-231).
- Panda, Pravati,Nayak, Sabita,Sahoo, Susanta Ku.,Mohapatra, Seetaram,Nayak, Deepika,Pradhan, Rajalaxmi,Kundu, Chanakya Nath
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p. 16802 - 16814
(2018/05/23)
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- A chromene pyrazoline derivatives fluorescent probe for Zn2+ detection in aqueous solution and living cells
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A new chromene pyrazoline derivatives fluorescent probe L was designed and synthesized. The probe L appears in a 55-fold fluorescence enhancement after 5 equiv. Zn2+ was added, and it also exhibits high sensitivity and selectivity for response
- Zhang, Ying-Peng,Xue, Qing-Hua,Yang, Yun-Shang,Liu, Xiao-Yu,Ma, Chun-Mei,Ru, Jia-Xi,Guo, Hui-Chen
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p. 128 - 134
(2018/05/04)
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- Bicatalytic Multistep Reactions En Route to the One-Pot Total Synthesis of Complex Molecules: Easy Access to Chromene and 1,2-Dihydroquinoline Derivatives from Simple Substrates
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By combining nanocatalysis with base catalysis, a novel one-pot multistep process was found for the synthesis of substituted heterocycles of biological relevance from simple substrates. The process is based on the initial Au/O2 oxidation of allylic alcohols, which is followed by base-catalyzed tandem hetero-Michael/aldolization/crotonization with ortho-hydroxy- or ortho-aminobenzaldehydes. The flexibility of the reaction even allowed the benzaldehyde partner to be prepared in situ in an example of a one-pot/five-step process.
- Giorgi, Pascal D.,Miedziak, Peter J.,Edwards, Jennifer K.,Hutchings, Graham J.,Antoniotti, Sylvain
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- Antimycobacterial activity of novel hydrazide-hydrazone derivatives with 2H-chromene and coumarin scaffold
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This study reports the synthesis of new 2H-chromene or coumarin based acylhydrazones, which were evaluated for their in vitro antimycobacterial activity against reference strain Mycobacterium tuberculosis H37Rv and compared to the first-line antituberculo
- Angelova, Violina T.,Valcheva, Violeta,Vassilev, Nikolay G.,Buyukliev, Rosen,Momekov, Georgi,Dimitrov, Ivan,Saso, Luciano,Djukic, Mirjana,Shivachev, Boris
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supporting information
p. 223 - 227
(2016/12/27)
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- Design and synthesis of (E)-4-(2-Phenyl-2H-chromen-3-yl)but-3-en-2-ones and evaluation of their in vitro antimicrobial activity
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2H-Chromene and its derivatives are an important class of organic compounds due to their wide range of biological activities such as antimicrobial, antiviral, antiimflamatory and antitubercular agents. In the present work we have synthesized ten new 2H-ch
- Nayak, Sabita,Chakroborty, Subhendu,Bhakta, Sujitlal,Panda, Pravati,Mohapatra, Seetaram,Kumar, Sanjeet,Jena, Padan Kumar,Purohit, Chandrasekhar
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p. 352 - 358
(2015/06/22)
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- Chiral diphenylperhydroindolinol silyl ether catalyzed domino oxa-Michael-aldol condensations for the asymmetric synthesis of benzopyrans
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Asymmetric domino oxa-Michael-aldol reactions between trans-cinnamaldehydes and salicylic aldehyde derivatives have been developed. Using (2S,3aS,7aS)-diphenylperhydro indolinol silyl ether 4i as the catalyst, most corresponding chiral benzopyrans can be
- Feng, Ya-Hui,Luo, Ren-Shi,Nie, Lin,Weng, Jiang,Lu, Gui
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p. 523 - 528
(2014/05/06)
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- Asymmetric Direct Michael Reactions of Cyclohexanone with Aromatic Nitroolefins in Water Catalyzed by Novel Axially Unfixed Biaryl-Based Bifunctional Organocatalysts
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A new family of axially unfixed biaryl-based water-compatible bifuctional organocatalysts were designed and synthesized for the asymmetric direct Michael reaction of cyclohexanone with various nitroolefins in water. One of the organocatalysts incorporates
- Zhao, Hong-Wu,Yang, Zhao,Yue, Yuan-Yuan,Li, Hai-Long,Song, Xiu-Qing,Sheng, Zhi-Hui,Meng, Wei,Guo, Xiao-Yu
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supporting information
p. 293 - 297
(2014/02/14)
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- Bifunctional acid-base ionic liquid for the one-pot synthesis of fine chemicals: Thioethers, 2H-chromenes and 2H-quinoline derivatives
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A bifunctional organocatalyst with ionic liquid properties and with an optimized distance between the acid and basic sites efficiently activates electron deficient olefins for 1,4 conjugated addition, which can be incorporated in different one-pot transformations for the preparation of cyclic and acyclic compounds of biological and synthetic interest. More specifically, the catalyst can be successfully applied for different carbon-carbon (CC) and carbon-heteroatom (C-N, C-O, C-S) bond forming reactions integrated in a cascade sequence. The activity of the organocatalyst has been compared with that of structurally related monofunctional and bifunctional catalysts. The most attractive features of this procedure are the high atom economy and the use of inexpensive starting materials as well as the use of an environmentally friendly catalyst that can be easily recovered due to its ionic liquid properties.
- Climent, Maria J.,Iborra, Sara,Sabater, Maria J.,Vidal, Juan D.
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- Asymmetric preparation of new N, N -dialkyl-2-amino-1,1,2-triphenylethanol catalysts and a kinetic resolution in the addition of diethylzinc to flavene-3-carbaldehydes
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Enantiopure N,N-dialkyl-(S)-2-amino-1,1,2-triphenylethanols were prepared using a new synthetic methodology and tested for their ability to catalyze the enantioselective addition of diethylzinc to aldehydes. The structural modification of N-substituents of the catalysts led us to identify N-methyl-N-(S)-1-phenyl-ethyl-substituted 4d as an effective catalyst for the addition. Also disclosed is a kinetic resolution of racemic flavene-3- carbaldehydes with the chiral catalyst.
- Kang, Seockyong,Baek, Jinho,Ko, Yikyung,Im, Chan,Park, Yongsun
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supporting information
p. 630 - 634
(2013/04/23)
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- Recyclable tertiary amine modified diarylprolinol ether as aminocatalyst for the sequential asymmetric synthesis of functionalized cyclohexanes and chromenes
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The one-pot, organocatalytic Hayashi sequential reaction (HSR) of β-nitroacrylate, aldehyde, toluenethiol, and ethyl 2-(diethoxyphosphoryl) acrylate allowed the synthesis of almost stereoisomerically pure, highly functionalized polysubstituted cyclohexane
- Shen, Hao,Yang, Ke-Fang,Shi, Zi-Hui,Jiang, Jian-Xiong,Lai, Guo-Qiao,Xu, Li-Wen
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experimental part
p. 5031 - 5038
(2011/10/12)
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- Chiral amine/chiral acid as an excellent organocatalytic system for the enantioselective tandem oxa-Michael-aldol reaction
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The asymmetric tandem oxa-Michael-aldol reaction of salicylic aldehyde derivatives with α,β-unsaturated aldehydes catalyzed by a chiral amine/chiral acid organocatalytic system was investigated. The organocatalytic system of (S)-diphenylpyrrolinol trimeth
- Luo, Shu-Ping,Li, Zhao-Bo,Wang, Li-Ping,Guo, Yi,Xia, Ai-Bao,Xu, Dan-Qian
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experimental part
p. 4539 - 4546
(2009/12/25)
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- One-pot pyrrolidine-catalyzed synthesis of benzopyrans, benzothiopyranes, and dihydroquinolidines
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A simple catalytic racemic synthesis of benzopyranes, benzothiopyranes and 1,2-dihydroquinolines is presented. The organocatalytic domino reactions between 2-heteroatom substituted aldehyde derivatives and α,β-unsaturated aldehydes or α,β-unsaturated cycl
- Ibrahem, Ismail,Sunden, Henrik,Rios, Ramon,Zhao, Gui-Ling,Cordova, Armando
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p. 219 - 223
(2008/02/04)
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