A. Arrieta et al., EFFICIENT TAUTOMERIZATION HYDRAZONE-AZOMETHINE IMINE UNDER MICROWAVE IRRADIATION - SYNTHESIS OF [4,3']BIPYRAZOLE AND [5,3']BIPYRAZOLE, Tetrahedron, 54(43), 1998, pp. 13167-13180
Microwave irradiation induces the thermal isomerization of pyrazolyl h
ydrazones to the corresponding azomethine imines which undergo 1,3-dip
olar cycloaddition with electron-poor dipolarophiles in a few min with
good yields. By classical heating, several dipolarophiles do not reac
t in comparable reaction conditions. Regiochemistry of bipyrazoles obt
ained from unsymmetrical dipolarophiles has been inferred by spectrosc
opic experiments. (C) 1998 Elsevier Science Ltd. All rights reserved.