Nitrobutadienes from β-nitrothiophenes:: valuable building-blocks in the overall ring-opening/ring-closure protocol to homo- or hetero-cycles

被引：41

作者：

Bianchi, Lara

Dell'Erba, Carlo

Maccagno, Massimo

Morganti, Stefano

Petrillo, Giovanni ^{[1
]}

Rizzato, Egon

Sancassan, Fernando

Severi, Elda

Spinelli, Domenico

Tavani, Cinzia

机构：

[1] Univ Genoa, Dipartimento Chim & Chim Ind, Via Dodecaneso 31, I-16146 Genoa, Italy

[2] Univ Bologna, Dipartimento Chim Organ A Mangini, I-40126 Bologna, Italy

来源：

ARKIVOC | 2006年

关键词：

nitrothiophenes; ring-opening; ring-closure; heterocycles; nitrobutadienes; isoxazoles;

D O I：

10.3998/ark.5550190.0007.714

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

beta-Nitrothiophenes undergo a facile ring-opening process when treated with secondary amines in ethanol ( in the presence of AgNO3, but for 3,4-dinitrothiophene), providing interesting polyfunctionalized linear nitro- or dinitro-butadienic building-blocks, which can be further manipulated and eventually exploited for the preparation of targets of various nature. In particular, a great variety of homo- and hetero-cyclic compounds may be obtained and some representative results in this field, relevant to synthetic, mechanistic and stereochemical aspects, are reported herein.

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页码：169 / 185

页数：17

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