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A new approach for the synthesis of some 1,4‐benzoxathiin 4,4‐dioxide derivatives
Author(s) -
Fan AiLong,
Cao Song,
Zhang Zheng
Publication year - 1997
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.5570340603
Subject(s) - chemistry , benzoxazole , potassium carbonate , aryl , dimethylformamide , aqueous solution , hydrogen peroxide , potassium hydroxide , tandem , medicinal chemistry , alkylation , sodium hydroxide , ammonium hydroxide , organic chemistry , solvent , catalysis , alkyl , materials science , composite material
A series of 1,4‐benzoxathiin 4,4‐dioxide derivatives have been prepared by a new synthetic route. The reactions of 2‐chloro‐4‐nitrobenzenethiol 1 with l‐aryl‐2‐chloroethanones 2 in the presence of sodium hydroxide give l‐aryl‐2‐(2‐chloro‐4‐nitrophenylthio)ethanones 3 which on oxidation with 30% aqueous hydrogen peroxide afford l‐aryl‐2‐(2‐chloro‐4‐nitrophenylsulfonyl)ethanones 4. By the reactions of compounds 4 with 2‐[3 or 4‐(bromomethyl)phenyl]benzoxazole in the potassium carbonate, triethylbenzyl‐ammonium chloride and dimethylformamide system, 2‐aryl‐3‐arylmethyl‐7‐nitro‐1,4‐benzoxathiin 4,4‐dioxides 5 or 6 are obtained via a tandem alkylation‐cyclization process.
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