Studies with functionally substituted N-alkylazoles: The reactivity of 1-(3,5-dimethylpyrazol-1-yl)-Acetone towards electrophilic reagents

Article abstract of DOI:10.1002/jhet.5570380324

The reaction of 1-(3,5-dimethylpyrazol-1-yl)acetone 4 with aromatic diazonium salts afforded the corresponding arylhydrazones 5a,b that were converted into pyridazines 6a,b and 8 via condensation with active methylene nitriles and dimethylformamide dimethylacetal, respectively. Condensation of 4 with phenylhydrazine afforded the phenylhydrazone 10, which could be converted into the indolylpyrazole 11 on treatment with ethanolic hydrochloric acid. Compound 4 also reacted with nitrous acid, benzylidenemalononitrile to yield a variety of substituted new pyrazoles.