Studies with Functionally Substituted Methylbenzotriazoles: Novel Synthesis of Functionally Substituted Pyrazolo[5,1‐c]‐1,2,4‐Triazines Benzotriazol‐1‐yl, 1‐Pyrazol‐4‐yl Benzotriazoles and 1‐Isoxazol‐4‐yl Benzotriazoles

Abstract 1‐Benzotriazolylacetophenone 1 couples with aromatic diazonium salts to yield the corresponding coupling products 2. Reaction of 1 with diazotized aminopyrazole afforded the benzotriazolylpyrazolo[5,1‐c][1,2,4]triazine 6. Compound 1 condensed with DMFDMA to yield the enaminone 7 which reacted with hydrazines to yield the pyrazoles 8a,b. Isomeric pyrazoles 10 were synthesized via condensing 1 with phenyl‐hydrazine and subsequent condensation of the formed phenylhydrazone 9 with DMFDMA. Reaction of 7 with hydroxylamine afforded the isoxazole 11 which was converted into the nitrile 13 on reflux in dioxane in the presence of sodium hydride. Compound 13 was also directly obtained from reaction of 1 with 1‐cyanobenzo‐triazole. The reaction of 1 with hippuric acid and arylidenemalononitriles 18a‐c afforded the pyranone 17 and pyridine derivatives 23a‐c, respectively.