Synthesis of novel heterocycles from 2-amino-3-(cyanomethylsulfonyl)thiophene

✍ Scribed by Chad E. Stephens; J. Walter Sowell Sr.

• Publisher: Journal of Heterocyclic Chemistry
• Year: 1998
• Tongue: English
• Weight: 458 KB
• Volume: 35
• Category: Article
• ISSN: 0022-152X
• DOI: 10.1002/jhet.5570350424

✦ Synopsis

Abstract

The synthesis and selected reactions of 2‐amino‐3‐(cyanomethylsulfonyl)thiophene is reported. In particular, cyclization reaction of the versatile aminothiophene yielded a number of novel thieno[3,2‐b][1,4]‐thiazine 1,1‐dioxides, as well as the analogous thieno[2,3‐e][1,3,4]thiadiazine 4,4‐dioxide. Reaction of the thienothiazine system with hydrazine was subsequently explored, which resulted in either ring‐opening of the thiazine and formation of an aminopyrazole or solely ring cleavage depending on the thiazine substituent. Additionally, the synthesis of bis(2‐amino‐3‐thienyl)sulfone and the corresponding bis‐acetamide is described.