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Synthesis of thieno[2,3-b][1,5]benzoxazepine derivatives

✍ Scribed by Toshiyuki Kohara; Hiroshi Tanaka; Koreichi Kimura; Hideki Horiuchi; Kohji Seio; Masafumi Arita; Tetsuya Fujimoto; Iwao Yamamoto

Publisher
Journal of Heterocyclic Chemistry
Year
2002
Tongue
English
Weight
104 KB
Volume
39
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

A new series of 4‐(4‐methylpiperazin‐1‐yl)thieno[2,3‐b][1,5]benzoxazepines 1a‐k has been synthesized from 4‐bromo‐2‐methylthiophene 6 or ethyl 2‐amino‐4,5‐dimethyl‐3‐thiophencarboxylate 10. Preparation of the key intermediate thieno[2,3‐b][1,5]benzoxazepine‐4(5__H__)‐ones 4a‐i, 4k were carried out by treatment of 2‐bromo‐N‐(2‐hydroxyphenyl)‐3‐thiophencarboxamides 5a‐i, 5k with potassium carbonate in DMSO. Compounds 1 are thienoanalogues of loxapine, a potent antipsychotic drug. Of these compounds, the neu‐roleptic activity of 2‐methyl‐4‐(4‐methylpiperazin‐l‐yl)thieno[2,3‐b][1,5]benzoxazepine 1a (R^1^, R^3^=H, R^2^=CH~3~) demonstrated potent antipsychotic activity.

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