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Synthesis 2012(2): 201-206  
DOI: 10.1055/s-0031-1289633
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A Facile One-Pot Synthesis of Substituted Thieno[2,3-b]pyridines from Enaminones

Baochang Gaoa,b, Dewen Dongb, Jie Zhanga, Changjiang Ding*a, Chunming Dongb, Yongjiu Liangb, Rui Zhang*b
a Department of Chemistry, Jilin University, Changchun 130012, P. R. of China
Fax: +86(431)85262676; e-Mail: ariel@ciac.jl.cn; e-Mail: dcjiang@163.com;
b Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun 130022, P. R. of China
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Publikationsverlauf

Received 7 September 2011
Publikationsdatum:
05. Dezember 2011 (online)

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Abstract

A facile and efficient one-pot synthesis of substituted thieno[2,3-b]pyridines has been developed. Treatment of enamin­ones, such as 2-acetyl-3-(dimethylamino)propenamides and -propenoates, with 2-cyanothioacetamide in the presence of potassium carbonate in N,N-dimethylformamide at 80 ˚C followed by addition of methylene-active bromides at room temperature provided, via intramolecular cyclization, 2,3,5,6-tetrasubstituted thieno[2,3-b]pyridines in yields of 78-90%. This protocol, which combines construction and modification of the thieno[2,3-b]pyridine ring, increases the structural diversity of the final products from readily available materials.

Key words

enaminones - cyclization - heterocycles - pyridine-2(1H)-thiones - thieno[2,3-b]pyridines

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