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Synthesis 2002(3): 0355-0360
DOI: 10.1055/s-2002-20033
PAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of a Benzo[5,6]cyclohepta[1,2-b]thiophene and Thieno[3,2-c]-benzazepine Derivatives

Toshiyuki Kohara*a, Hiroshi Tanakaa, Koreichi Kimuraa, Tetsuya Fujimotob, Iwao Yamamotob, Masafumi Aritaa
a Exploratory Research I (CNS), Pharmaceuticals Research Division, Mitsubishi Pharma Corporation, 7-25 Koyata 3-Chome, Iruma, Saitama 358-0026, Japan
Fax: +81(42)9641906; e-Mail: Kohara.Toshiyuki@mh.m-pharma.co.jp ;
b Department of Functional Polymer Science, Faculty of Textile Science and Technology, Shinshu University, 15-1 Tokida 3-Chome, Ueda, Nagano 386-8567, Japan
Further Information

Publication History

Received 23 October 2001
Publication Date:
28 July 2004 (online)

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Abstract

A new series of 2-methyl-4-(4-methylpiperazin-1-yl)-10H-benzo[5,6]cyclohepta[1,2-b]thiophene (5) and 2-methyl-4-(4-methylpiperazin-1-yl)thieno[3,2-c][1]benzazepine derivatives 6b-f have been synthesized from 2-methylthiophene and phthalic anhydride. Preparation of the key intermediate 2-methyl-4,5-dihydro-10H-benzo[5,6]cyclohepta[1,2-b]thiophene-4-one (12) and 2-methylthieno[3,2-c][1]benzazepine-4(5H),10-dione (16) were carried out by intramolecular dehydration of the phenylacetic acid 11 and Lewis acid associated cyclization of the isocyanate 14, respectively.

Key words

cyclization - Curtius rearrangement - antipsychotic agents

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