Reactivity of Functionally Substituted Azoles Towards Electrophiles. Novel Synthesis of Thienylazoles and Phenylazoles

Abstract

Phenacyl bromide reacted with imidazole 1a and 1,2,4-triazole 1b to yield the respective azolylacetophenones 1c,d. These reacted with phenyl isothiocyanate and phenacyl bromide yielding thienylazoles 4a,b. Reaction of 1c,d with dimethylformamide dimethylacetal followed by treating of the product with thiourea afforded the azolylpyrimidines 10a,b. Azolylpyrans 8a,b were obtained from reaction of 1c,d with acrylonitrile. The reaction of azoles 1a,b with chloroacetylacetone in acetone solution in the presence of base afforded the phenylazoles 13a,b.