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Synthesis and reactions of N‐Aryl‐C‐arylsulfonylformohydrazidoyl bromides
Author(s) -
Hassaneen Hamdi M.,
Abdelhamid Abdou O.,
Fahmi Abdelgawad A.,
Shawali Ahmad S.
Publication year - 1985
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.5570220235
Subject(s) - chemistry , morpholine , acetic anhydride , sodium ethoxide , ethyl acetoacetate , acetylacetone , acetic acid , potassium thiocyanate , aryl , organic chemistry , sodium acetate , medicinal chemistry , halogenation , ethanol , pyrazole , piperidine , catalysis , alkyl
Abstract Bromination of 1‐arylsulfonyl‐1,2‐propanedione‐1‐aryl‐hydrazones 7 in a mixture of acetic acid and acetic anhydride in the presence of sodium acetate gave N ‐aryl‐ C ‐arylsulfonylformohydrazidoyl bromides 5. Treatment of 5 with dibenzoylmethane, acetylacetone, ethyl acetoacetate and ethyl benzoylacetate in ethanol in the presence of sodium ethoxide yielded the pyrazole derivatives 8‐11 , respectively. Reaction of 5 with potassium thiocyanate afforded the thiadiazoline derivative 14. The bromides 5 also react with nucleophiles such as morpholine, piperidine, phenoxide, thiophenoxide and benzenesulfinate anions to give the corresponding substitution products 19‐23 , respectively. The structures of the products 8‐23 were assigned and confirmed on the basis of their spectral and elemental analyses, their chemical behaviour and alternate synthesis wherever possible.