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Reaction of 2‐Phenyl‐4‐arylidene‐1,3‐oxazolones with Different Nucleophiles for Synthesis of Some New Heterocycles
Author(s) -
Youssef A. S. A.,
ElMariah F. A.,
AbdElmottaleb F. T.,
Hashem H. E.
Publication year - 2019
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.3419
Subject(s) - chemistry , malononitrile , benzamide , piperidine , derivative (finance) , phenyl isothiocyanate , medicinal chemistry , organic chemistry , ammonium acetate , diethyl malonate , schiff base , ethyl acetoacetate , carbohydrazide , stereochemistry , catalysis , high performance liquid chromatography , financial economics , economics
Refluxing of 1,3‐oxazolone ( 1a ) with malononitrile in dry benzene and in the presence of ammonium acetate afforded imidazolone derivative ( 2 ). However, carrying out the same reaction in absolute ethanol and in the presence of piperidine as a base gave the benzamide derivative ( 4 ). Fusion of ( 1a ) with p ‐anisidine gave the open adduct benzamide ( 6 ), which cyclized in acidic medium to give imidazolone derivative ( 7 ). Heating of imidazolone ( 7 ) with malononitrile above its melting point afforded 1,3‐diazepine derivative ( 8 ). Reaction of the carbohydrazide ( 9 ) with isatin in ethanol gives the corresponding Schiff base ( 11 ), which then reacted with acetyl acetone, ethyl acetoacetate, ethyl cyanoacetate, and malononitrile in n ‐butanol and piperidine to afford benzamide derivative ( 13 , 14 , 15 ) and ( 16 ), respectively. The structures of the newly synthesized compounds were established on the basis of IR, 1 H‐NMR, mass spectra, and elemental analyses.