Reaction of 1-Nitro-2, 2'-bismethylthioethylene. III. Reaction of Methyl 1-Cyano-2-methylthio-3-nitrocrotonate with Hydrochloric Acid

Sone, M.; Tominaga, Yoshinori; Natsuki, Reiko; Matsuda, Yoshiro; Kobayashi, Gorô

doi:10.1248/yakushi1947.93.8_1008

Cited by 7 publications

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“…The methylation of 3a-d with dimethyl sulfate in the presence of sodium hydroxide in dimethyl sulfoxide (DMSO) readily gave the corresponding dimethyl products (4a-d), which were readily converted to 1-methyl-4-methylthio-1H-pyrrole-2, 5-diones (5a-d) in good yields by hydrolysis with concentrated hydrochloric acid in methanol. Hydrolysis of 3b with hydrochloric acid solution in refluxing methyl cellosolve gives 4-methylthio-3-methoxycarbonylmaleimide (6) in 40% yield [6].…”

Section: Synthesis Of 4-methylthiomaleimidesmentioning

confidence: 99%

“…Compound 9 was also readily obtained by dealing with 7 in hydrochloric acid [6]. We also tried to obtain 5-aryl-4-methylthiomaleimides (3-aryl-4-methylthio-1H-pyrrole-2,5-diones) by using the reaction of nitroketene dithioacetal (1e) with aryl acetonitriles.…”

Section: Synthesis Of 4-methylthiomaleimidesmentioning

confidence: 99%

“…1,3-Disubstituted compound (45d) was obtained from 44c in 91% yield. Compounds 45d, e, and f were synthesized by reactions of 47a-c with hydrazine hydrate under refluxing in methanol in 78,82,and 76% yields,3':5,6]pyrido[2,3-d]pyridazine-5,8(6H,7H)-diones (45d-f) showed nearly the same or somewhat stronger light intensity than luminol at pH 8.0. The unsubstituted compounds 3b, c did not show CL at pH 8.0.…”

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ChemInform Abstract: Synthesis of Methylthiomaleimides for the Preparation of Pyridazines and Related Compounds.

2002

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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.

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Section: Synthesis Of 4-methylthiomaleimidesmentioning

confidence: 99%

Section: Synthesis Of 4-methylthiomaleimidesmentioning

confidence: 99%

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