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A facile synthesis of new thieno[2,3-b][1,4]thiazine derivatives starting from 2-acylamino-3,3-dichloroacrylonitriles

✍ Scribed by Sergey V. Popil'nichenko; Vladimir S. Brovarets; Alexander N. Chernega; Denis V. Poltorak; Boris S. Drach

Publisher
John Wiley and Sons
Year
2006
Tongue
English
Weight
110 KB
Volume
17
Category
Article
ISSN
1042-7163

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✦ Synopsis

Readily available 2-acylamino-3,3dichloroacrylonitriles are sequentially treated with methyl mercaptoacetate in the presence of sodium methylate and with sulfuric acid to furnish the methyl ester of 7-amino-2-oxo-3H-thieno [2,3-b][1,4]thiazine-6-carboxylic acid. Treating it first with triethyl orthoformate and then with ammonia or primary amines, the pyrimidine-4-one nucleus is annelated to the thienothiazine system, which is corroborated by spectroscopic methods and X-ray diffraction analysis.

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