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Acetylenic ketones. Part VI . Reaction of aroylphenylacetylenes with hydrazine derivatives
Author(s) -
Baddar F. G.,
AlHajjar F. H.,
ElRayyes N. R.
Publication year - 1978
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570150306
Subject(s) - chemistry , acetophenone , acetic anhydride , methylhydrazine , potassium hydroxide , hydrazine (antidepressant) , dimethylhydrazine , sodium hydroxide , organic chemistry , medicinal chemistry , acetic acid , ketone , catalysis , phenylhydrazine , medicine , colorectal cancer , chromatography , cancer
The reaction of aroylphenylacetylenes (I) with acyl‐ or aroylhydrazines (II) gave ω‐aroyl‐acetophenone‐ N ‐acyl or N ‐aroylhydrazones (IV). The latter gave upon treatment with methanolic potassium hydroxide and with acetic anhydride in the presence of sodium acetate, the corresponding pyrazoles (V) and the N ‐acetylpyrazoles (VII and VIII), respectively. The acetylenic ketones ( 1 ) also reacted with methylhydrazine and 1,1‐dimethylhydrazine to give 5‐aryl‐1‐methyl‐3‐phenylpyrazoles (XII), and 1,1‐dimethylhydrazine derivatives (XIII), respectively. When the latter compounds were heated with acetic anhydride, they gave the N ‐methylpyrazoles (XII).