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Synthesis and structural characterisation of 4H-1,3-benzothiazine derivatives

✍ Scribed by Lajos Fodor; Gábor Bernáth; Jari Sinkkonen; Prof. Kalevi Pihlaja

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

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✦ Synopsis

Abstract

The ring‐closure reactions of N‐arylthiomethylaroylamide derivatives (1a‐g) in the presence of phospho ‐rus oxychloride gave 2‐aryl‐4__H__‐1,3‐benzo‐thiazines (2a‐g). 2‐(3‐Chlorophenyl)‐6‐methyl‐4__H__‐1,3‐benzoth‐iazine (2b) was reduced with Zn to obtain the corresponding 2,3‐dihydro derivative (3b). Potassium permanganate oxidation of 2‐(4‐chlorophenyl)‐2,3‐diethoxy‐4__H__‐ (2e) and 2‐(2‐fluorophenyl)‐6,7‐diefhoxy‐4__H__‐1,3‐benzo‐thiazines (2g) gave the corresponding 4‐ones (4e,g). The reactions of 2‐(4‐chlorophenyl)‐6‐mefhyl‐4__H__‐1,3‐benzofhiazine (2c) with substituted acetyl chlorides led to linearly condensed ß‐lactams (5a,b). The structures of the compounds studied were confirmed by ^1^H and ^13^C NMR and by their characteristic mass spectrometric fragmentations.

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