Regio-orientation in condensation of aminopyrazoles with 1,3-difunctional reagents: synthesis of new pyrazolo[1,5-a]pyrimidines; pyrazolo[3,4-d]pyridazines and 2,4-dihydropyrano[2,3-c]pyrazoles

Pyrazolo [1,5-a]pyrimidine derivatives were prepared by condensation of 4-phenyldiazenyl-1Hpyrazole-3,5-diamine with enaminonitriles and with enaminones.The regioorientation of reagents was determined by ( 15 N HMBC) measurements as well as NOE difference experiments.A new one-pot synthesis of pyrazolo[3,4-d]pyridazines involving the coupling of N1-[4-cyano-5(3)-(cyanomethyl)-1H-3(5)pyrazoly]acetamide with benzenediazonium chloride is reported.Synthesis of 2,4-dihydropyrano[2,3-c]pyrazole is also reported.

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