Studies with Polyfunctionally Substituted Heteroaromatics: The Reaction of Heterocyclic Enaminonitriles with α‐β‐Unsaturated Nitriles

5‐Amino‐4‐cyano‐3‐phenylpyrazole ( 1 ) reacts with cinnamonitriles ( 2 ) to yield the pyrazolo[1,5‐a]pyrimidines ( 3 ). Also, 5‐amino‐4‐cyano‐1‐phenylpyrazole ( 4 ) reacts with cinnamonitriles ( 2 ) to yield the pyrazolo[3,4‐b]pyridine derivatives ( 5 ). In contrast to this reaction, enaminothiophene ( 6 ) reacts with cinnamonitriles ( 2 ) to yield compound ( 7 ) not ( 8 ). The enaminopyrane ( 9 ) reacts with cinnamonitriles ( 2 ) to yield ( 10 ). Finally we have attempted to add cinnamonitriles ( 2 ) to thiopyrane ( 13 ); only rearrangement and aromatization product ( 14 ) was isolated.     

Utility of β‐(4‐Chlorobenzoyl)acrylic Acid in Heterocyclic Synthesis

β‐(4‐Chlorobenzoyl)acrylic acid (1) proved to be a convenient precursor for the synthesis of a variety of heterocyclic systems through the reaction with compounds containing active methylene groups under Michael reaction conditions. Also, the reactivity of Michael adduct towards nitrogen nucleophiles was investigated to afford diazepine, indazole, isoxazole and quinazoline derivatives. Some of the synthesized compounds were screened for their biological activity.