Reactions of isocyanates with methyl N-(cyanothioformyl)anthranilate

✍ Scribed by L. M. Deck; E. P. Papadopoulos; K. A. Smith

• Publisher: Journal of Heterocyclic Chemistry
• Year: 2003
• Tongue: English
• Weight: 77 KB
• Volume: 40
• Category: Article
• ISSN: 0022-152X
• DOI: 10.1002/jhet.5570400522

✦ Synopsis

Abstract

The triethylamine‐catalyzed reactions of methyl N‐(cyanothioformyl)anthranilate (1) with isocyanates result in cyclization involving the cyano group to form methyl 2‐(4‐imino‐2‐oxo‐3‐substituted‐5‐thioxoimi‐dazolidin‐1‐yl)benzoates (4). Ring closure at the ester carbonyl to form 3‐aryl‐3,4‐dihydro‐4‐oxoquinazo‐line‐2‐carbonitriles (8) is observed when the S‐methyl derivative of 1 is allowed to react with aromatic amines.