Synthesis of thieno[2,3-c]- and thieno[3,2-c]-azepinones

Kyosuke Satake, Kenji Itoh, Yoshiko Miyoshi, Masaru Kimura, Shiro Morosawa

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6 Citations (Scopus)

Abstract

The 7-benzyl-5,6,7,8-tetrahydro-4H-thieno[2,3-c]azepin-4-one (11) has been synthesized from the N-benzyl-N-(2-thenyl)-β-alanine (10) by a tin(IV) chloride-catalysed Friedel-Crafts cyclization. In addition, N-benzyl- and N-(p-tolylsulphonyl)-N-(3-thenyl)-β-alanine (16a) and (16b) cyclized more effectively to give 5-benzyl- and 5-(p-tolylsulphonyl)-4,5,6,7-tetrahydro-8H- thieno[3,2-c]azepin-8-one (17a) and (17b), respectively. Attempts to remove the p-tolylsulphonyl group from compound (17b) was achieved by use of polyphosphoric acid (PPA) and afforded the 4,5,6,7-tetrahydro-8H-thieno[3,2-c]azepin-8-one (19). In contrast, 7-bromo-5-(p-tolylsulphonyl)-4,5,6,7-tetrahydro-8H-thieno-[3, 2-c]azepin-8-one (20) gave the novel heterocyclic system, 6,7-dihydroazirino[1, 2-a]-thieno[2,3-d]pyridin-8-one (22) under similar conditions.

Original languageEnglish
Pages (from-to)729-732
Number of pages4
JournalJournal of the Chemical Society, Perkin Transactions 1
Publication statusPublished - Dec 1 1986

ASJC Scopus subject areas

  • Chemistry(all)

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    Satake, K., Itoh, K., Miyoshi, Y., Kimura, M., & Morosawa, S. (1986). Synthesis of thieno[2,3-c]- and thieno[3,2-c]-azepinones. Journal of the Chemical Society, Perkin Transactions 1, 729-732.