Collection of Czechoslovak Chemical Communications · 1990 · 13 citations · 0 references
Natural SciencesChemistryMedicinal ChemistryCatalysisOrganic ChemistrySynthetic Medicinal ChemistryHeterocycle SynthesisHeterocyclic ChemistryHeterocyclic CompoundsOrganic SynthesisHeterocyclic AromaticityPyrazine ChemistryPyrazole ChemistryPyrazole SynthesisPyridine ChemistryPyridine SynthesisQuinoline SynthesisThiazole Chemistry
3-Amino-4-cyanopyrazole I reacts with hydroxylamine and with hydrazine to yield 1 H ,6 H -3-aminopyrazolo[3,4- c ]pyrazole ( III and IV ). Diazotized IV couples with 2-naphthol to give the arylazo derivative VI which cyclizes to 9 H -naphthol[2,1- e ]pyrazolo[3',4':3,4]pyrazolo[5,1- c ]-[1,2,4]triazine VII by means of acetic acid. The pyrazol-5-ylthiourea obtained from I and phenyl isothiocyanate undergoes base-catalyzed cyclization to give pyrazolo[3,4- d ]pyrimidinethione derivative IX . Compound I reacts with cyclohexane in the presence of zinc chloride to give the tetrahydropyrazolo[3,4- b ]quinoline derivative XI . The reaction of I with pyridine 1-oxide affords 4 H ,5 H -pyrazolo[5',1':2,3] [1,2,4]triazolo[1,5- a ]pyridine-3-carbonitrile XII .