A New, One-Pot, Multicomponent Synthesis of Bioactive N-Pyrazolylformamidines under Microwave Irradiation

Dedicated to Professor Viktor E. Kolla on the occasion of his 90^th birthday

Abstract

A one-pot, three-component, microwave-assisted reaction of polysubstituted 5-aminopyrazoles, triethyl orthoformate, and a series of cyclic secondary amines was developed and successfully employed for the synthesis of novel N-pyrazolylformamidines. Under catalyst-free conditions, the reaction proceeded in a chemo- and regioselective manner, resulting in the formation of unsymmetric formamidines, which were isolated in high yields and purity. Some of the prepared compounds were found to inhibit interleukin-17 secretion in phenotypic in vitro assays.

Key words

formamidines - pyrazoles - orthoesters - multicomponent reaction - microwave-assisted synthesis

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