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Synthesis of 2-acetonyl-, 2-phenacyl-, and 2-(dioxocycloalkyl)-substituted thieno[2,3-d][1,3]thiazin-4-ones

✍ Scribed by Gütschow, Michael ;Leistner, Siegfried

Publisher: John Wiley and Sons
Year: 1995
Tongue: English
Weight: 413 KB
Volume: 1995
Category: Article
ISSN: 0947-3440
DOI: 10.1002/jlac.199519950258

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✦ Synopsis

Abstract

The reaction of ethyl 2‐isothiocyanato‐3‐thiophenecarboxylates 1 with anions of acyclic as well as of cyclic 1,3‐diketones or diethyl malonate affords diacylthioacetamide derivatives 2. Upon treatment with concd. sulfuric acid 2a‐1 are transformed into novel 2‐substituted thieno[2.,3‐d][1,3]thiazin‐4‐ones 3a‐j. Ring cleavage of 3a‐f with sodium alkoxides gives N‐(3‐alkoxycarbonyl‐2‐thienyl)thioacetamides 4a‐h.

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