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Preparation of 1,5‐disubstituted 4‐sulfonylpyrazoles, β‐cyano‐β‐sulfonylenamines and 5‐substituted 4‐sulfonylisoxazoles from β‐keto‐β‐sulfonylenamines
Author(s) -
Takahashi Masahiko,
Mamiya Tsutomu,
Hasegawa Hisao,
Nagai Takashi,
Wakita Hideki
Publication year - 1986
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.5570230520
Subject(s) - chemistry , hydroxylamine , ring (chemistry) , butyllithium , medicinal chemistry , organic chemistry , stereochemistry
Reaction of β‐keto‐β‐sulfonylenamines 1a,b with N ‐substituted hydrazines gave 1,5‐disubstituted 4‐sulfonylpyrazoles 2a‐h in moderate yields, which were ring‐opened on treatment with n ‐butyllithium to afford β‐cyano‐β‐sulfonylenamines ( 3a,b,d‐f ). 5‐Substitued 4‐sulfonylisoxazoles 6a‐d were also prepared from 1a‐d and hydroxylamine.