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Studies with enamines and azaenamines: Synthesis and reactivity of 3‐dimethylamino‐2‐[(3‐indolyl) carbonyl]propenonitrile
Author(s) -
Abdallah Tayseer A.
Publication year - 2007
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.5570440436
Subject(s) - chemistry , yield (engineering) , enamine , hydrazine (antidepressant) , acetic acid , ethyl acetoacetate , ammonium acetate , medicinal chemistry , pyrazole , organic chemistry , hydrate , ammonia , dimethylformamide , formamide , reactivity (psychology) , catalysis , chromatography , medicine , materials science , high performance liquid chromatography , alternative medicine , pathology , solvent , metallurgy
2‐Oxo‐3‐(indol‐3‐yl)propanonitrile 2 condensed with dimethylformamide dimethylacetal to yield the enaminonitrile 3 . The latter reacted with 4‐chloroaniline to yield the 4‐chlorophenylaminoacrylonitrile 5 . Reaction of 3 with hydrazine hydrate led to formation of pyrazole‐4‐carbonitrile 6 . Compound 3 reacted with ethyl acetoacetate in refluxing acetic acid and in presence of ammonium acetate to yield the indolylpyridine 10 . Enamine 3 reacted with 5(1 H )‐aminotriazole 13 and 3(5)‐aminopyrazole 17 to yield the pyrimidine derivatives 15 and 19 , respectively.