Synthesis of methylthiomaleimides for the preparation of pyridazines and related compounds

Yoshinori Tominaga, Yasuhiro Shigemitsu, Kenji Sasaki

Research output: Contribution to journalArticle

21 Citations (Scopus)

Abstract

New functionalized maleimides (3-methylthio-2,5-dioxo-1H-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 maleimides reacted with various nucleophilic reagents such as electron-rich aromatic and heteroaromatic compounds like dialkylanilines, aminophenols, indoles, indolizines, and cyalazines to give the corresponding 3-aryl- or heteroaryl-1H-pyrole-2,5-diones. Styryl and merocyanine dyes, and polycyclic pyridazine-diones as chemiluminophors and succinimides were also obtained from these maleimides with good results.

Original languageEnglish
Pages (from-to)571-591
Number of pages21
JournalJournal of Heterocyclic Chemistry
Volume39
Issue number3
Publication statusPublished - 2002
Externally publishedYes

Fingerprint

Pyridazines
Maleimides
Indolizines
Succinimides
Aminophenols
Indoles
Pyrroles
Dimethyl Sulfoxide
Methanol
Electrons
ketene

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Synthesis of methylthiomaleimides for the preparation of pyridazines and related compounds. / Tominaga, Yoshinori; Shigemitsu, Yasuhiro; Sasaki, Kenji.

In: Journal of Heterocyclic Chemistry, Vol. 39, No. 3, 2002, p. 571-591.

Research output: Contribution to journalArticle

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