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Reaction of substituted sulfenes with N,N ‐disubstituted α‐amino‐methyleneketones. II. Synthesis of N,N ‐disubstituted cis and trans 4‐amino‐3‐chloro‐3,4,5,6,7,8‐hexahydro‐1,2‐benzoxathiin 2,2‐dioxides, and 4‐amino‐5,6,7,8‐tetrahydro‐1,2‐benzoxathiin 2,2‐dioxides
Author(s) -
Bargagna Alberto,
Sche Pietro,
Bignardi Gaetano,
Longobardi Mario
Publication year - 1983
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.5570200622
Subject(s) - chemistry , triethylamine , adduct , medicinal chemistry , benzene , chloride , amino acid , cycloaddition , stereochemistry , organic chemistry , catalysis , biochemistry
The polar 1,4‐cycloaddition of chlorosulfene (generated in situ from chloromethanesulfonyl chloride and triethylamine) to N,N ‐disubstituted (E)‐2‐aminomethylenecyclohexanones I gave mixtures of N,N ‐disubstituted cis and trans 4‐amino‐3‐chloro‐3,4,5,6,7,8‐hexahydro‐1,2‐benzoxathiin 2,2‐dioxides III and IV, except for N,N ‐diphenyl enaminone which did not react. Only compounds IV could be separated from these mixtures by silica gel chromatography, with the exception of the piperidino adducts (III + IV)d, from which also IIId could be obtained pure. Compounds IV or mixtures III + IV were dehydrochlorinated with DBN in refluxing benzene to afford N,N ‐disubstituted 4‐amino‐5,6,7,8‐tetrahydro‐1,2‐benzoxathiin 2,2‐dioxides V in satisfactory yields. Structural and conformational features of compounds III, IV and V were determined from uv, ir and nmr spectral data.