Studies with polyfunctionally substituted heteroaromatics: The reaction ofheterocyclic enaminonitriles with alpha-beta-unsaturated nitriles

5-Amino-4-cyano-3-phenylpyrazole (1)reacts with cinnamonitriles (2) to yiel d the pyrazolo[1,5-a]pyrimidines (3). Also, 5-amino-4-cyano-1-phenylpyrazol e (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 arom atization product (14) was isolated.