β-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.
Nitrobutadienes from β-nitrothiophenes: valuable building-blocks in the overall ring-opening / ring-closure protocol to homo- or hetero-cycles
BIANCHI, LARA;DELL'ERBA, CARLO;MACCAGNO, MASSIMO;PETRILLO, GIOVANNI;SANCASSAN, FERNANDO;TAVANI, CINZIA
2006-01-01
Abstract
β-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.File in questo prodotto:
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