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Synthesis 2009(22): 3803-3806  
DOI: 10.1055/s-0029-1217019
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Efficient Methods for the Synthesis of Thieno[3,2-b]thiophene and Thieno[3,2-b]furan Derivatives

Valerii Z. Shirinian*, Alexey A. Shimkin, Stepan N. Tipikin, Mikhail M. Krayushkin
N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991 Moscow, Russian Federation
Fax: +7(499)1355328; e-Mail: shir@ioc.ac.ru;
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Publication History

Received 18 June 2009
Publication Date:
23 September 2009 (online)

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Abstract

A novel approach to the synthesis of thieno[3,2-b]thiophenes and thieno[3,2-b]furans bearing various substituents from readily accessible starting materials has been developed. The methodology is based on C- and O-alkylation of ethyl 4-hydroxy-2-methylthiophene-3-carboxylate with α-halo ketones, followed by cyclization.

Key words

alkylation - cyclization - heterocycles - thienothio­phenes - thienofurans

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