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Some Reactions of Chalcone‐4‐Sulfonyl Chloride and 4‐Methoxychalcone‐3‐Sulfonyl Chloride
Author(s) -
Cremlyn Richard J.,
Swinbourne Frederick J.,
Shode Olufemi O.
Publication year - 1984
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.198400054
Subject(s) - sulfonyl , chemistry , phenylhydrazine , chalcone , hydrazine (antidepressant) , nucleophile , chloride , organic chemistry , medicinal chemistry , catalysis , alkyl , chromatography
Chalcone and 4‐methoxychalcone react with chlorosulfonic acid to give chalcone‐ p ‐sulfonyl chloride and 4‐methoxchalcone‐3‐sulfonyl chloride respectively. The sulfonyl chlorides were converted into 13 sulfonyl derivatives by reaction with nucleophiles. With hydrazine and phenylhydrazine the chalconesulfonyl chlorides were cyclised to the corresponding hydrazinopyrazolines. In contrast, with N,N‐dimethyl‐hydrazine only the dimethylsulfonohydmides were obtained, and no attack on the carbonyl group was observed. Possible reasons for this difference in behaviour are discussed, together with spectroscopic evidence for the structures proposed.