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Cyclization reactions of 2‐(2‐chloro‐4‐nitrophenylsulfonyl)‐1‐(2‐thienyl)ethanone
Author(s) -
Fan AiLong,
Cao Song,
Xu JingHua,
Zhang Zheng
Publication year - 1998
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.5570350237
Subject(s) - chemistry , tandem , dimethylformamide , sulfonyl , solvent , medicinal chemistry , alkylation , acrylate , base (topology) , organic chemistry , catalysis , polymer , mathematical analysis , materials science , alkyl , monomer , mathematics , composite material
A new sulfonyl group‐containing heterocyclic compound 2‐(2‐chloro‐4‐nitrophenylsulfonyl)‐1‐(2‐thienyl)ethanone 2 was prepared from the corresponding sulfide 2‐(2‐chloro‐4‐nitrophenylthio)‐1‐(2‐thienyl)ethanone 1 . Two different cyclization reactions of the compound 2 were discussed. In contrast to the tandem alkylation‐cyclization process [1], another cyclic procedure was described. In the presence of 1,8‐diazabicyclo[5.4.0]undec‐7‐ene as a base and dimethylformamide as a solvent, compound 2 was treated with ethyl acrylate or methyl methacrylate at 50–55° to give the 1,4‐benzoxathiin 4,4‐dioxide 5 or 6 respectively via a tandem Michael conjugate addition‐cyclization process.