(E)-3-Halo-2-styryl-4H-chromen-4-ones: synthesis and transformation to novel pyrazoles

New methods for the synthesis of (E)-3-halo-2-styryl-4H-chromen-4-ones were established. The reaction of these compounds with hydrazine hydrate afforded new and unexpected 3(5)-aryl-5(3)-[2-(2-hydroxyphenyl)-2-hydrazonoethyl]-1H-pyrazoles, which upon acid hydrolysis gave 3(5)-aryl-5(3)-[2-(2-hydroxyphenyl)-2-oxoethyl]-1H-pyrazoles. The reaction mechanisms for these transformations, involving 1,6- followed by 1,4-conjugate additions, are discussed and the structures of all new compounds were established by NMR studies.