Heterocyclic synthesis with nitriles: Synthesis of some new thiocyanato-substituted heterocycles from alkylidene malononitrile

✍ Scribed by Fathy M. Abdelrazek

• Book ID: 102228901
• Publisher: John Wiley and Sons
• Year: 1995
• Tongue: English
• Weight: 291 KB
• Volume: 6
• Category: Article
• ISSN: 1042-7163
• DOI: 10.1002/hc.520060305

✦ Synopsis

a-(Thiocyanatomethyl)benzylidenemalononitrile undergoes bromination with N-bromo succinimide to afford a-(bromothiocyanatomethy1)benzylidene- malononitrile. This bromo derivative undergoes reactions with sodium hydrogen sulfide, thioglycollic acid, hydroxylamine hydrochloride, phenylhydrazine, and hydrazine hydrate to afford thiophene, 4H-thiopyran, 4H-oxazine, pyridazine, and bis(thiazo1-2-ylidene)azine derivatives, respectively. Mechanistic ex- planations as well as structure elucidations are discussed.