Reaction of 4-aryl-3-thiosemicarbazides with carbon disulfide: A facile synthesis of 2,3-dihydrothiazoles and their fused derivatives

✍ Scribed by Rafat M. Mohareb; Sherif M. Sherif

• Publisher: John Wiley and Sons
• Year: 1997
• Tongue: English
• Weight: 203 KB
• Volume: 8
• Category: Article
• ISSN: 1042-7163
• DOI: 10.1002/(sici)1098-1071(1997)8:1<77::aid-hc13>3.0.co;2-1

✦ Synopsis

The reaction of 3-aryl-3-thiosemicarbazides 1a-d with carbon disulfide in alkaline medium affords the nonisolable sulfide salts 2a-d. The latter undergo in situ heterocyclization with some ␣-halogenated compounds, e.g., 3a,b and 13, to afford polyfunctionally substituted 2,3-dihydrothiazoles 4a-e and thiazolidine 14, respectively, which, in turn, could be annelated into fused heterocyclic systems. Chemical and spectroscopic evidence for the new compounds are described.