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Reaction of substituted sulfenes with N,N ‐disubstituted α‐amino‐methyleneketones. I. Synthesis of N,N ‐disubstituted cis ‐ and trans ‐4‐amino‐3,4,5,6,7,8‐hexahydro‐3‐phenyl‐1,2‐benzoxathiin 2,2‐dioxides
Author(s) -
Bargagna Alberto,
Bignardi Gaetano,
Sche Pietro,
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.5570200402
Subject(s) - chemistry , triethylamine , adduct , cycloaddition , alkyl , medicinal chemistry , stereochemistry , column chromatography , chloride , nuclear magnetic resonance spectroscopy , catalysis , organic chemistry
The polar 1, 4‐cycloaddition of phenylsulfene (generated in situ from phenylmethanesulfony] chloride and triethylamine) to N, N ‐disubstituted ( E )‐2‐aminomethylenecyclohexanones I gave in general a mixture of N, N ‐disubstituted cis ‐ and trans ‐4‐amino‐3, 4, 5, 6, 7, 8‐hexahydro‐3‐phenyl‐1, 2‐benzoxathiin 2, 2‐dioxides III and IV, which were separated by column chromatography and whose structural and conformational features were determined from uv, ir and nmr spectral data. In the case of N, N ‐diisopropylamino enaminone 1c, the cyclo‐addition took place with elimination of an alkyl group as propene to give the adduct IIIℓ.