Abstract
Glyoxalbis(phenylhydrazone) 1a reacts with aromatic aldehydes and secondary amines to yield either propan-1,2-dialdiphenylhydrazones 2 or arylazopyrazoles 7 depending on the nature of utilised aldehyde. The reactivity of 1a with phosphorus oxychloride (POCl3) and dimethylformamide (DMF) (Vilsmeier reaction) afforded the cinnolin-3-carbaldehyde phenylhydrazone 11. Compound 1a afforded also the tribenzoyl derivative 16 on treatment with benzoyl chloride. Only the diacetyl derivative 17 was produced on refluxing 1a in acetic anhydride. The diphenylhydrazone 20 was produced on treatment of 19, prepared via coupling 18 with benzenediazonium chloride followed by phenylhydrazine. This cyclised into pyrazole 21 on reflux in acetic acid.
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