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

被引:53
作者
Babu, A. R. Suresh [1 ]
Raghunathan, R. [1 ]
机构
[1] Univ Madras, Dept Chem, Madras 600025, Tamil Nadu, India
关键词
D O I
10.1016/j.tetlet.2006.10.139
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient synthesis of dispiroindenoquinoxaline pyrrolizidine derivatives has been expediently accomplished by a one-pot four component 1,3-dipolar cycloaddition reaction. High regioselectivity was achieved using heteropolyacid H-4[Si(W3O10)(3)]-silica as a catalyst. X-ray diffraction studies of one of the cycloadducts proved the structure and regiochemistry of the cycloadduct. (c) 2006 Elsevier Ltd. All rights reserved.
引用
收藏
页码:9221 / 9225
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]  
BAILLY C, 1909, ANTICANCER DRUG RES, V15, P291
[7]  
BAN Y, 1976, CHEM PHARM BULL, V24, P736
[8]  
BAN Y, 1975, CHEM PHARM BULL, V23, P2605
[9]  
BAN Y, 1974, TETRAHEDRON LETT, P187
[10]   Unexpected cycloadducts from 1,3-dipolar cycloaddition of 3,4-dehydromorpholine N-oxide to N-cinnamoyl piperidines-first report of the novel formation of 2:1 cycloadducts [J].
Banerji, A ;
Bandyopadhyay, D ;
Prangé, T ;
Neuman, A .
TETRAHEDRON LETTERS, 2005, 46 (15) :2619-2622