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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