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Paper | Regular issue | Vol 63, No. 6, 2004, pp.1281-1298
Published online, 20th April, 2004
DOI: 10.3987/COM-04-10020
Chemistry of Polyhalogenated Nitrobutadienes, 1: A New Synthesis of Perfunctionalized 3-Amino-4-nitrothiophenes

Viktor A. Zapol′skii, Jan C. Namyslo, Arnold E. W. Adam, and Dieter E. Kaufmann*

*Institute of Organic Chemistry, Technical University of Clausthal, Leibnizstrasse 6, D-38678 Clausthal-Zellerfeld, Germany

Abstract

An efficient synthesis of perfunctionalized 3-amino-4-nitrothiophenes was developed starting from highly chlorinated 2-nitrobutadiene derivatives. The key step of this new approach is the cyclization reaction of highly nucleophilic, ω-chlorinated butadienyl thiolates generated from 2-(2-diorganylamino-3,3-dichloro-1-nitroallylidene)-[1,3]dithiolanes upon action of base.