Access to 3-arylmethyl-5-(methylthio)isoxazoles via an initial ring-opening of 2-methylthio-4-nitrothiophene

被引：17

作者：

Bianchi, L ^{[1
]}

Dell'Erba, C ^{[1
]}

Gabellini, A ^{[1
]}

Novi, M ^{[1
]}

Petrillo, G ^{[1
]}

Tavani, C ^{[1
]}

机构：

[1] Univ Genoa, Dipartimento Chim & Chim Ind, I-16146 Genoa, Italy

来源：

TETRAHEDRON | 2002年 / 58卷 / 17期

关键词：

nitrothiophenes; ring-opening/ring-closure reactions; functionalized nitrobutadienes; 3,5-disubstituted isoxazoles;

D O I：

10.1016/S0040-4020(02)00292-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reactions of 1, 1 -bis(methylthio)-3-nitro-4-pyrrolidino-1.3-butadiene (deriving from the initial ring-opening of 2-methylthio-4-nitrothiophene with pyrrolidine and silver nitrate in EtOH) with arylmagnesium bromides result in the chemoselective replacement of the pyrrolidino group with the aryl moiety of the Grignards. The 4-aryl-1,1-bis(methylthio)-3-nitro-1,3-butadienes thus obtained are the key intermediates for the effective synthesis, through the corresponding reduction products 4-aryl-3-hydroximino-1, 1-bis(methylthio)-1-butenes, of the previously unknown 3-arylmethyl-5-(methylthio)isoxazoles. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：3379 / 3385

页数：7

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