Synthesis of novel spiropyrrolidine/pyrrolizine-oxindole scaffolds through 1,3-dipolar cycloadditions

被引：50
作者：
Ghandi, Mehdi [1 ]
Yari, Ahmad [1 ]
Rezaei, Seyed Jamal Tabatabaei [1 ]
Taheri, Abuzar [1 ]
机构：
[1] Univ Tehran, Univ Coll Sci, Sch Chem, Tehran, Iran
来源：
TETRAHEDRON LETTERS | 2009年 / 50卷 / 33期
关键词：
Sarcosine; Azomethine ylide; Spirooxindole; Cycloaddition; ONE-POT SYNTHESIS; AZOMETHINE YLIDES; INHIBITORS;
D O I：
10.1016/j.tetlet.2009.06.033
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The one-pot, three-component condensation of sarcosine or proline Schiff bases with several aromatic alclehydes and the Knoevenagel adduct of isatin-malononitrile successfully affords spiropyrrolidine-oxindoles and spiropyrrolizine-oxindoles. (C) 2009 Elsevier Ltd. All rights reserved.
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收藏
页码：4724 / 4726
页数：3
相关论文
共 17 条
[1]   Synthesis and evaluation of some new spiro indoline-based heterocycles as potentially active antimicrobial agents [J].
Abdel-Rahman, AH ;
Keshk, EM ;
Hanna, MA ;
El-Bady, SM .
BIOORGANIC & MEDICINAL CHEMISTRY, 2004, 12 (09) :2483-2488
[2]  
ABOUGHARBIA MA, 1979, HETEROCYCLES, V12, P637
[3]   Ultrasonic assisted-silica mediated [3+2] cycloaddition of azomethine ylides - a facile multicomponent one-pot synthesis of novel dispiroheterocycles [J].
Babu, A. R. Suresh ;
Raghunathan, R. .
TETRAHEDRON LETTERS, 2007, 48 (38) :6809-6813
[4]   ZrOCl2•8H2O mediated microwave induced [3+2] cycloaddition of azomethine ylides -: a facile one-pot synthesis of novel dispiroheterocycles [J].
Babu, A. R. Suresh ;
Raghunathan, R. .
TETRAHEDRON LETTERS, 2007, 48 (02) :305-308
[5]   CONFORMATIONALLY RESTRICTED INHIBITORS OF THE HIGH-AFFINITY L-GLUTAMATE TRANSPORTER [J].
BRIDGES, RJ ;
LOVERING, FE ;
HUMPHREY, JM ;
STANLEY, MS ;
BLAKELY, TN ;
CRISTOFARO, MF ;
CHAMBERLIN, AR .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1993, 3 (01) :115-&
[6]   Intramolecular dipolar cycloaddition reactions of azomethine ylides [J].
Coldham, I ;
Hufton, R .
CHEMICAL REVIEWS, 2005, 105 (07) :2765-2809
[7]  
Cordell G.A., 1998, The Alkaloids: Chemistry and Biology
[8]   Novel mammalian cell cycle inhibitors, spirotryprostatins A and B, produced by Aspergillus fumigatus, which inhibit mammalian cell cycle at G2/M phase [J].
Cui, CB ;
Kakeya, H ;
Osada, H .
TETRAHEDRON, 1996, 52 (39) :12651-12666
[9]   2-Oxoindolin-3-ylidene derivatives as 2π components in 1,3-dipolar cycloadditions of azomethine ylides [J].
Fejes, I ;
Nyerges, M ;
Szöllosy, A ;
Blaskó, G ;
Toke, L .
TETRAHEDRON, 2001, 57 (06) :1129-1137
[10]  
FRIEBOLIN H, 1993, BASIC 1 2 DIMENSIONA, P52
12