Reaction of 1-Nitro-2, 2-bis(methylthio)ethylene. II. Synthesis of 2-Hydroxyimino-3-methylthio-5-oxopyrroline Derivatives

• Published in: Chemical & pharmaceutical bulletin Vol. 21; no. 8; pp. 1667 - 1675
• Main Authors: SONE, MASAKATSU, MATSUDA, YOSHIRO, TOMINAGA, YOSHINORI, KOBAYASHI, GORO, NATSUKI, REIKO
• Format: Journal Article
• Language: English
• Published: Tokyo The Pharmaceutical Society of Japan 1973; Japan Science and Technology Agency
• ISSN: 0009-2363; 1347-5223; 1347-5223
• DOI: 10.1248/cpb.21.1667

Methyl 1-cyano-2-methylthio-3-nitrocrotonate, 1-phenyl-2-methylthio-3-nitrocrotonitrile, and 1-cyano-2-methylthio-3-nitrocrotonamide, which contain cyano and nitro group at 1-and 3-position, were refluxed in MeOH or EtOH to give 2-hydroxy-3-methylthio-5-oxopyrroline derivatives, with ring closure between cyano and nitro group. The reaction of methyl 1-cyano-2-methylthio-3-nitrocrotonate with equimolar amount of amine gave methyl 2-hydroxy-3-amino-5-oxopyrroline-4-carobxylate which was replaced methylthio with amino group and with ring closure. However, with excess amine gave amine salt of nitro group, and also replaced with methylthio group. The raction of pyrroline derivatives with active methylene compounds gave the corresponding substituted compounds.