A facile one-pot domino reaction for the stereoselective synthesis of acryl derivatives promoted by Ca(OTf)2

被引：8

作者：

Yaragorla, Srinivasarao ^{[1
]}

Saini, Pyare Lal ^{[1
]}

Pareek, Abhishek ^{[1
]}

Almansour, Abdulrahman I. ^{[2
]}

Arumugam, Natarajan ^{[2
]}

机构：

[1] Cent Univ Rajasthan, Organ & Med Chem Lab, Dept Chem, NH-8, Ajmer 305817, Rajasthan, India

[2] King Saud Univ, Dept Chem, Coll Sci, POB 2455, Riyadh 11451, Saudi Arabia

来源：

TETRAHEDRON LETTERS | 2016年 / 57卷 / 19期

关键词：

beta-Enamino ester; Indolyl acrylates; Oxindolyl acrylates; Domino reactions; Heterocyclic compounds; Calcium catalysis; MULTICOMPONENT REACTIONS; 4-COMPONENT REACTIONS; AROMATIC-ALDEHYDES; METHYL PROPIOLATE; ARYLAMINES; CHEMISTRY; OXINDOLES; CONSTRUCTION; HETEROCYCLES; INHIBITORS;

D O I：

10.1016/j.tetlet.2016.03.098

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A facile one-pot domino reaction for the stereoselective synthesis of acryl derivatives has been reported using alkaline earth catalyst [Ca(OTf)(2)]. Initially aryl amine reacts with ethyl propiolate to form 6-enamino ester which further reacts with aryl aldehyde and indole in the presence of Ca(OTf)(2) to give indolyl acrylates. It is interesting to note that in the absence of indole the reaction leads to the formation of benzylidene bisacrylates. Similarly 6-enamino ester reacts with another electrophilic partner isatin in the presence of Ca(OTf)(2) to give oxindolyl acrylates. The products were isolated in good yields by simple filtration. (C) 2016 Elsevier Ltd. All rights reserved.

引用

页码：2034 / 2038

页数：5

共 49 条

[1] A simple and effective approach to the synthesis of rhodanine derivatives via three-component reactions in water
Alizadeh, Abdolati
Rostamnia, Sadegh
Zohreh, Nasrin
Hosseinpour, Reza
[J]. TETRAHEDRON LETTERS, 2009, 50 (14) : 1533 - 1535
[2] A new one-pot three-component condensation reaction for the synthesis of 2,3,4,6-tetrasubstituted pyridines
Bagley, MC
Dale, JW
Bower, J
[J]. CHEMICAL COMMUNICATIONS, 2002, (16) : 1682 - 1683
[3] Targeting Structural and Stereochemical Complexity by Organocascade Catalysis: Construction of Spirocyclic Oxindoles Having Multiple Stereocenters
Bencivenni, Giorgio
Wu, Li-Yuan
Mazzanti, Andrea
Giannichi, Berardino
Pesciaioli, Fabio
Song, Mao-Ping
Bartoli, Giuseppe
Melchiorre, Paolo
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (39) : 7200 - 7203
[4] [2+2] Cycloaddition of electron-poor acetylenes to (E)-3-dimethylamino-1-heteroaryl-prop-2-en-1-ones: synthesis of highly functionalized 1-heteroaroyl-1,3-butadienes
Bezensek, Jure
Kolesa, Tanja
Groselj, Uros
Wagger, Jernej
Stare, Katarina
Meden, Anton
Svete, Jurij
Stanovnik, Branko
[J]. TETRAHEDRON LETTERS, 2010, 51 (26) : 3392 - 3397
[5] Efficient Organocatalytic Dual Activation Strategy for Preparing the Versatile Synthons (2E)-1-(Het)Aryl/styryl-3-(dimethylamino)prop-2-en-1-ones and α-(E)-[(Dimethylamino)methylene]cycloalkanones
Bindal, Sachin
Kumar, Dinesh
Kommi, Damodara N.
Bhatiya, Sonam
Chakraborti, Asit K.
[J]. SYNTHESIS-STUTTGART, 2011, (12): : 1930 - 1935
[6] Bronsted acid-promoted domino reactions: a novel one-pot three-component synthesis of 3,4,5-trisubstituted-3,6-dihydro-2H-1,3-oxazines
Cao, Hua
Jiang, Huan-Feng
Qi, Chao-Rong
Yao, Wen-Juan
Chen, Huo-Ji
[J]. TETRAHEDRON LETTERS, 2009, 50 (11) : 1209 - 1214
[7] Catalytic asymmetric synthesis of 3,3-disubstituted oxindoles: diazooxindole joins the field
Cao, Zhong-Yan
Wang, Yu-Hui
Zeng, Xing-Ping
Zhou, Jian
[J]. TETRAHEDRON LETTERS, 2014, 55 (16) : 2571 - 2584
[8] Multi-component syntheses of heterocycles by transition-metal catalysis
D'Souza, Daniel M.
Mueller, Thomas J. J.
[J]. CHEMICAL SOCIETY REVIEWS, 2007, 36 (07) : 1095 - 1108
[9] Pd-Catalyzed Assembly of Spirooxindole Natural Products: A Short Synthesis of Horsfiline
Deppermann, Nina
Thomanek, Heike
Prenzel, Alexander H. G. P.
Maison, Wolfgang
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (17) : 5994 - 6000
[10] Dinesh K., 2012, EUR J ORG CHEM, V32, P6407

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