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Amine‐induced lossen rearrangements of 3‐hydroxy‐5,6‐dihydrouracil and N ‐hydroxysuccinimide benzenesulfontes
Author(s) -
VanVerst Mary E.,
Bell Charles L.,
Bauer Ludwig
Publication year - 1979
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.5570160708
Subject(s) - chemistry , aniline , butylamine , piperidine , amine gas treating , benzene , medicinal chemistry , acylation , chloride , chloroacetyl chloride , organic chemistry , ammonia , catalysis
The reaction of sodium succinohydroxamate with benzenesulfonyl chloride yielded 3‐benzene‐sulfonyloxy‐5,6‐dihydrouracil, 3 . Treatment of 3 with ammonia, aniline, t ‐butylamine or piperidine yielded a mixture of the requisite 1,2‐bis(ureido)ethane and 1‐curboxamido‐2‐imidazolidone. Acylation of N ‐hydroxysuccinimide with benzenesulfonyl chloride furnished N ‐benzenesulfonyl‐oxysuccinimide, 10. Aniline or t ‐butylamine were used as representative amines to demonstrate their capability of inducing a Lossen degradation on 10 to afford the corresponding β‐ ureido ‐propionamide.