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Efficient One-Pot Synthesis of Highly Substituted Thiophene Library from 1,3-Dicarbonyl Compounds

By Wang Y, Huang J, Chai YY, Liu Q, Liang YJ and Dong DW*

Abstract

A faccile and efficient one-pot synthesis of highly substituted thiophenes has been developed and employed for the preparation of a small focused library. Treatment of 1,3-dicarbonyl compounds 1 with CS2 in the presence of K2CO3 in DMF at room temperature, followed by stepwise addition of alkyl bromides 2 and methylene active bromides 3, provided via intramolecular cyclization 2,3,4,5-tetrasubstituted thiophenes 4 in yields of 77-94%. This protocol, combining construction and modification of the thiophene ring, increases the structural diversity of final products from readily available materials. A mechanism for the one-pot synthesis of thiophenes of type 4 has been proposed. A small focused library of thiophenes is prepared using the sequential addition of reagents to achieve unique substitution in the 2 and 5 position of the thiophene rin

Topics: OXO KETENE DITHIOACETALS, TETRASUBSTITUTED THIOPHENES, CONVENIENT SYNTHESIS, PRACTICAL SYNTHESIS, ORGANIC-SYNTHESIS, CARBON-DISULFIDE, GEWALD REACTION, SOLID-SUPPORT, ANNULATION, FACILE, Organic synthesis, Carbon disulfide, Carbon bisulfide, Carbon disulphide, Dithiocarbonic anhydride, BISULFURE DE CARBONE, SCHWEFELKOHLENSTOFF
Year: 2008
DOI identifier: 10.1021/cc800015b
OAI identifier: oai:ir.ciac.jl.cn:322003/9701
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