Synthesis of monofluorinated indolizines and their derivatives by the 1,3-dipolar reaction of N-ylides with fluorinated vinyl tosylates

被引：81

作者：

Fang, X

Wu, YM

Deng, J

Wang, SW

机构：

[1] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Organofluorine Chem, Shanghai 200032, Peoples R China

[2] Anhui Normal Univ, Dept Chem, Wuhu Anhui 241000, Peoples R China

来源：

TETRAHEDRON | 2004年 / 60卷 / 25期

关键词：

1,3-dipolar reaction; N-ylides; fluorinated vinyl tosylate; monofluorinated indolizines and derivatives; synthesis;

D O I：

10.1016/j.tet.2004.04.012

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Monofluorinated indolizines 4, benzo[d]indolizines 7 and 4H-pyrrolo[1,2-a]benzimidazoles 8 were synthesized in moderate yields by 1,3-dipolar reaction between fluorinated vinyl tosylates 2a and N-ylides of pyridinium, isoquinolinium and benzimidazolinium, generated in situ from their halides salts. When the same N-ylides were allowed to react with 2,3,3-trifluoro-1-propenyl tosylate 2b, the unexpected product formylated indolizines and their derivatives 9 were obtained. The reaction mechanism is also proposed. (C) 2004 Elsevier Ltd. All rights reserved.

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页码：5487 / 5493

页数：7

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