Synthesis and cyclization reactions of 2-amino-3-[(methoxy-carbonyl)methylsulfonyl]pyrroles and thiophene

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

• Book ID: 102892865
• Publisher: Journal of Heterocyclic Chemistry
• Year: 1998
• Tongue: English
• Weight: 525 KB
• Volume: 35
• Category: Article
• ISSN: 0022-152X
• DOI: 10.1002/jhet.5570350425

✦ Synopsis

Abstract

The title aminopyrroles and thiophene have been prepared by condensation of methyl (cyanomethyl‐sulfonyl)acetate with various α‐amino ketones or 2‐mercaptoacetaldehyde, respectively. Subsequent cyclization of these compounds by reaction between the amine and activated methylene has led to various ester‐substituted thiazine‐ and thiadiazine‐based bicyclic derivatives. In addition, cyclization of the title compounds by intramolecular coupling of the amine and ester has led to the analogous bicyclic thiazin‐3(2__H__)‐ones. Attempted hydrolysis of the ester‐substituted bicyclics to the corresponding carboxylic acids was unsuccessful.