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Synthesis 2011(18): 2897-2906  
DOI: 10.1055/s-0030-1260152
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of 3-Arylthieno[2,3-b]-, -[2,3-c]- or -[3,2-c]pyridines Utilizing an Interrupted Pummerer Reaction

Kazuhiro Kobayashi*, Teruhiko Suzuki, Mai Horiuchi, Yasuhiko Shiroyama, Hisatoshi Konishi
Division of Applied Chemistry, Department of Chemistry and Biotechnology, Graduate School of Engineering, Tottori University, 4-101 Koyama-minami, Tottori 680-8552, Japan
Fax: +81(857)315263; e-Mail: kkoba@chem.tottori-u.ac.jp;
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Publikationsverlauf

Received 20 May 2011
Publikationsdatum:
05. August 2011 (online)

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Abstract

An efficient procedure for the synthesis of three types of thienopyridines has been developed. Thus, 3-(1-arylethenyl)-2-(ethylsulfinyl)pyridines, 4-(1-arylethenyl)-3-(ethylsulfinyl)pyridines, and 3-(1-arylethenyl)-4-(ethylsulfinyl)pyridines, which can be easily prepared from the respective aryl chloropyridinyl ketones in a three-step sequence, undergo an interrupted Pummerer reaction on treatment with excess acetic anhydride at temperatures ranging from 100 to 130 ˚C to give 3-arylthieno[2,3-b]pyridines, 3-aryl­thieno[2,3-c]pyridines, and 3-arylthieno[3,2-c]pyridines, respectively.

Key words

thieno[2,3-b]pyridines - thieno[2,3-c]pyridines - thieno[3,2-c]pyridines - interrupted Pummerer reaction - acetic anhydride

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