An efficient one-pot synthesis of 6-aryl-5-cyano-2-thiopyrimidinone derivatives and their piperidinium ionic forms, x-ray crystal structures

✍ Scribed by Saeed Balalaie; Morteza Bararjanian; Frank Rominger

• Publisher: Journal of Heterocyclic Chemistry
• Year: 2006
• Tongue: English
• Weight: 438 KB
• Volume: 43
• Category: Article
• ISSN: 0022-152X
• DOI: 10.1002/jhet.5570430402

✦ Synopsis

Abstract

magnified image

Three‐component condensation of benzaldehyde derivatives, alkyl cyanoacetates and thiourea in the presence of piperidine in reflux condition provides a direct route to piperidinium 6‐aryl‐5‐cyano 2‐thiopyrimidonate salts in good yields. These reactions were also carried out under microwave irradiation. The yields of products under the microwave condition were better as compared to the reflux media. The acidification of these ionic forms resulted in the formation of 6‐aryl‐5‐cyano‐2‐thiopyrimidone derivatives. The X‐ray structures of the ionic forms (4, 5, and 7) show that there are anionic thiopyrimidinone skeletons hydrogen bridged with piperidinium cations.