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Studies with enaminonitriles: Synthesis and chemical reactivity of 2‐phenyl‐3‐piperidin‐1‐yl acrylonitrile under microwave heating
Author(s) -
Salaheldin Abdellatif M.,
Alphy Maryana K.
Publication year - 2008
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570450202
Subject(s) - chemistry , yield (engineering) , hydrazine (antidepressant) , acrylonitrile , reagent , quinoline , methylene , organic chemistry , hydrate , piperidine , cyanide , reactivity (psychology) , amine gas treating , medicinal chemistry , medicine , materials science , chromatography , copolymer , pathology , metallurgy , polymer , alternative medicine
Benzyl cyanide reacts with triethylorthoformate and piperidine in DMF solution to yield the title compound 2 . This reacted with aromatic amines to yield either aminoacrylonitriles or quinoline depending on reaction conditions and substitution pattern on the aromatic amine. The reaction of compound 2 with hydrazine hydrate could only be effected in the microwave oven and resulted in the formation of aminopyrazole 7 . Diazotization of 7 and coupling with an active methylene reagent afforded pyrazolo[5,1‐ c ]‐[1,2,4]triazine derivatives.