Imidazoline-4-thiones from cyanothioformamides and aldehyde imines: Formation, aromatization, and acetylation

✍ Scribed by Ahmed M. Sh. El-Sharief; Roger Ketcham; Monika Ries; Ernst Schaumann; Gunadi Adiwidjaja

• Book ID: 102343047
• Publisher: Journal of Heterocyclic Chemistry
• Year: 2010
• Tongue: English
• Weight: 139 KB
• Volume: 47
• Category: Article
• ISSN: 0022-152X
• DOI: 10.1002/jhet.333

✦ Synopsis

Abstract

magnified image The reaction of N‐methyl‐ (3a) or N‐phenylcyanothioformamide (3b**)** with acetaldimine (5a, as 1‐amino‐1‐ethanol) gives 5‐(amino)imidazolidine‐4‐thiones 6B. Product 6a reacts with a second equivalent of 3a to give 8 which in turn is oxidized to disulfide 9. Using araldimines 5b,5c, only 1:2 intermediates 10 derived from 3a, 3b and two moles of the imine 5 are formed, but proved to be easily oxidized to disulfides 11. Acetylation of 6 occurs chemoselectively on the exocyclic nitrogen and finally also on the thione sulfur to give 14 via 13. J. Heterocyclic Chem., (2010).