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A convenient synthesis of the novel 5H-thieno[2,3-e]-4,1,2-oxathiazepine ring system via an alkoxycarbenium ion intermediate

✍ Scribed by Anura P. Dantanarayana; Brian Dupre; Jesse A. May; Vincent M. Lynch

Publisher
Journal of Heterocyclic Chemistry
Year
1999
Tongue
English
Weight
763 KB
Volume
36
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

3‐(Methoxymethoxymethyl)‐2‐thiophenesulfonamides and 3‐hydroxymethyl‐N‐methoxymethyl‐2‐thiophenesulfonamides have been shown to undergo cyclization when treated under anhydrous acidic conditions to provide the novel 2,3‐dihydro‐5__H__‐thieno[2,3‐e]‐4,1,2‐oxathiazepine ring system. Incorporation of a primary sulfonamide group into position seven of the molecule provided compounds which inhibit human carbonic anhydrase II.

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