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Sythesis of methylthiomaleimides for the preparation of pyridazines and related comopounds
Author(s) -
Tominaga Yoshionori,
Shigemitsu Yasuhiro,
Sasaki Kejni
Publication year - 2002
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.5570390312
Subject(s) - chemistry , nitromethane , ketene , pyridazine , succinimides , reagent , nucleophile , organic chemistry , methylene , medicinal chemistry , dimethyl sulfoxide , methanol , aryl , catalysis , alkyl
New functionalized maleimides (3‐methylthio‐2,5‐dioxo‐1 H ‐pyrroles) were obtained by the reaction of ketene dithioacetals with nitromethane or the reaction of nitro ketene dithioacetal with active methylene compounds in the presence of the appropriate base in dimethyl sulfoxide followed by treatment with methanol. These nakeunudes reacted with various nucleophilic reagents such as election‐rich aromatic and heteroaromatic compounds like dialkylanilines, aminophenols, indoles, indolizines, and cyalazines to give the corresponding 3‐aryl‐ or heteroaryl‐ 1 H ‐pyrole‐2,5‐diones. Styryl and merocyanie dyes, and polycyclic pyridazine‐diones as chemiluminophors and succinimides were also obtained from these maleimides with good results.