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Synthesis 2004(1): 75-79  
DOI: 10.1055/s-2003-44358
PAPER
© Georg Thieme Verlag Stuttgart · New York

New Efficient Synthesis of 2-Substituted 5,6,7,8-Tetrahydro-benzo­thieno[2,3-d]pyrimidin-4(3H)-ones

Ming-Wu Ding*, Shang-Jun Yang, Jing Zhu
Institute of Organic Synthesis, Central China Normal University, Wuhan, 430079, P. R. China
Fax: +86(27)87876070; e-Mail: ding5229@yahoo.com.cn;
Further Information

Publication History

Received 19 September 2003
Publication Date:
03 December 2003 (online)

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Abstract

The carbodiimides 4, obtained from aza-Wittig reactions of iminophosphorane 3 with aromatic isocyanates, reacted with secondary amines to give 2-dialkylamino-5,6,7,8-tetrahydro-benzothieno[2,3-d]pyrimidin-4(3H)-ones 6 in presence of catalytic EtO-Na+. Reactions of 4 with phenols or ROH in presence of catalytic K2CO3 or RO-Na+ gave 2-aryl(alkyl)oxy-5,6,7,8-tetrahydro-benzothieno[2,3-d]pyrimidin-4(3H)-ones 6 in satisfactory yields. The effects of the nucleophiles on cyclization have been investi­gated.

Key words

benzothieno[2,3-d]pyrimidin-4(3H)-ones - iminophosphorane - carbodiimide - aza-Wittig reaction - synthesis

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