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Acetylenic ketones. Part V . Reaction of acetylenic ketones with thiourea and some of its 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.5570150122
Subject(s) - chemistry , phenylhydrazine , thiourea , hydrazine (antidepressant) , hydrate , medicinal chemistry , pyrimidine , aryl , acetylation , disulfide bond , organic chemistry , stereochemistry , alkyl , biochemistry , chromatography , gene
Aroylphenylacetylenes (I) reacted with thiourea and S ‐benzylisothiourea to give 4,6‐diaryl‐pyrimidine‐2(1 H )thiones (IV) and α‐aroyl‐β‐benzylmercaptostyrenes (X), respectively. Methyla‐tion and acetylation of the thiones (IV) gave the corresponding S ‐methyl‐ (V) and S‐acetyl‐ (VI) derivatives, respectively. The oxidation of these thiones gave the corresponding disulfide derivatives (VII). Reaction of α‐aroyl‐β‐benzylmercaptostyrenes (X) with hydrazine hydrate and phenylhydrazine gave 3(5)‐aryl‐5(3)‐phenylpyrazoles (XI) and 3‐aryl‐1,5‐diphenylpyrazoles (XIII), respectively. Reaction of aroylphenylacetylenes (1) with N ‐allylthiourea gave 1‐allyl‐4,6‐diaryl‐pyrimidine‐2‐thiones (XVI).