Ultrasonic assisted-silica mediated [3+2] cycloaddition of azomethine ylides - a facile multicomponent one-pot synthesis of novel dispiroheterocycles

被引:69
作者
Babu, A. R. Suresh [1 ]
Raghunathan, R. [1 ]
机构
[1] Univ Madras, Dept Organ Chem, Madras 600025, Tamil Nadu, India
关键词
D O I
10.1016/j.tetlet.2007.07.085
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient synthesis of dispiro-oxindolopyrrolizidine and dispirooxindolothienopyrrole derivatives has been expediently accomplished via a one-pot, three-component 1,3-dipolar cycloaddition reaction. High regioselectivity was achieved on ultrasonication in the presence of silica as a catalyst. X-ray diffraction studies of one of the cycloadducts proved the structure and regiochemistry of the cycloaddition. (c) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码:6809 / 6813
页数:5
相关论文
共 45 条
[1]  
AMALRAJ A, 2003, BIOORGAN MED CHEM, V11, P407
[2]  
Amalraj A., 2001, TETRAHEDRON, V57, P10293, DOI DOI 10.1016/S0040-4020(01)01042-0
[3]  
[Anonymous], 1989, Adv. Heterocycl. Chem, DOI DOI 10.1016/S0065-2725(08)60332-3
[4]  
[Anonymous], 1984, 13 DIPOLAR CYCLOADDI
[5]   A novel access to highly functionalised β-lactams by regio- and stereoselective 1,3-dipolar cycloaddition reaction [J].
Arumugam, N ;
Jayashankaran, J ;
Manian, RDRS ;
Raghunathan, R .
TETRAHEDRON, 2005, 61 (35) :8512-8516
[6]   Heteropolyacid-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, 2006, 47 (52) :9221-9225
[7]  
Bailly C, 1999, ANTI-CANCER DRUG DES, V14, P291
[8]  
BAN Y, 1976, CHEM PHARM BULL, V24, P736
[9]  
BAN Y, 1975, CHEM PHARM BULL, V23, P2605
[10]  
BAN Y, 1974, TETRAHEDRON LETT, P187