1,3-Dipolar cycloreversion of a 1,3,4-oxadiazolidine as a controlled azomethine imine surrogate for pyrazolidine synthesis

被引:45
作者
Khau, VV [1 ]
Martinelli, MJ [1 ]
机构
[1] LILLY CORP CTR,LILLY RES LABS,CHEM PROC R&D,INDIANAPOLIS,IN 46285
关键词
D O I
10.1016/0040-4039(96)00836-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Azomethine imines were generated in a controlled manner through a thermally allowed 1,3-dipolar cycloreversion of 1,3,4-oxadiazolidilles and subsequently trapped with dipolarophiles. This method results in the construction of the pyrazolidine heterocycles. A new method for the selective formation of the key semicarbazide substrate, from benzylidene hydrazone, is also disclosed. Copyright (C) 1996 Elsevier Science Ltd.
引用
收藏
页码:4323 / 4326
页数:4
相关论文
共 20 条
[1]   CONFORMATIONAL-ANALYSIS OF SATURATED HETEROCYCLES .70. NITROGEN INVERSIONS IN 1,3,4-OXADIAZOLIDINES [J].
BAKER, VJ ;
KATRITZKY, AR ;
MAJORAL, JP .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1975, (11) :1191-1193
[2]   1,3-DIPOLAR CYCLOREVERSIONS [J].
BIANCHI, G ;
DEMICHELI, C ;
GANDOLFI, R .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1979, 18 (10) :721-738
[3]   ELECTRON-IMPACT INDUCED FRAGMENTATIONS MIMICKING RETRO-1,3-DIPOLAR CYCLOADDITIONS [J].
HAMMERUM, S ;
WOLKOFF, P .
JOURNAL OF ORGANIC CHEMISTRY, 1972, 37 (24) :3965-&
[4]  
Huisgen R., 1964, CHEMISTRY ALKENES, P739
[5]  
Huisgen R., 1984, 1 3 DIPOLAR CYCLOADD, P1
[6]  
Huisgen R., 1988, ADV CYCLOADDITION, V1, P1
[7]   TOTAL SYNTHESIS OF (+/-)-SAXITOXIN [J].
JACOBI, PA ;
MARTINELLI, MJ ;
POLANC, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (19) :5594-5598
[8]  
KELLY TR, 1972, SYNTH-INT J METHODS, P544
[9]   A NEW SYNTHESIS OF DL-GLUTAMINE [J].
KLINE, GB ;
COX, SH .
JOURNAL OF ORGANIC CHEMISTRY, 1961, 26 (06) :1854-&
[10]  
OPPOLZER W, 1970, TETRAHEDRON LETT, V25, P2199