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Synthesis 2014; 46(24): 3319-3330
DOI: 10.1055/s-0034-1379011
DOI: 10.1055/s-0034-1379011
paper
A Convenient and Efficient Synthesis of 2-(Het)arylthieno[3,2-b]pyridin-7(4H)-ones and 2,3-Di(het)arylthieno[3,2-b]pyridin-7(4H)-ones
Further Information
Publication History
Received: 01 June 2014
Accepted after revision: 01 August 2014
Publication Date:
28 August 2014 (online)
Abstract
A simple and efficient synthesis of 2-aryl-3-hydroxythieno[3,2-b]pyridin-7(4H)-ones, 7-methoxy-2,3-diarylthieno[3,2-b]pyridines, and 2,3-diarylthieno[3,2-b]pyridin-7(4H)-ones is presented. The synthesis involves thioalkylation of methyl 4-methoxypicolinate at the 3-position, followed by cyclization in situ to give 2-aryl-7-methoxythieno[3,2-b]pyridin-3-ols. Demethylation of these compounds gives the corresponding 2-arylthieno[3,2-b]pyridin-7(4H)-ones. Further functionalization of 7-methoxy-2-arylthieno[3,2-b]pyridin-3-ols was achieved by converting the hydroxy group into the corresponding triflate, which underwent palladium-catalyzed cross-coupling to give 7-methoxy-2,3-di(het)arylthieno[3,2-b]pyridines. Subsequent demethylation of the 7-methoxy group gave the corresponding pyridinones.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/products/ejournals/journal/ 10.1055/s-00000084.
- Supporting Information
Primary Data
- for this article are available online at http:// www.thieme-connect.com/products/ejournals/journal/10.1055/s-00000084 and can be cited using the following DOI: 10.4125/pd0060th.
- Primary Data
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