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Report | Regular issue | Vol 22, No. 8, 1984, pp.1733-1739
Published online, 1st January, 1970
DOI: 10.3987/R-1984-08-1733
Pseudoesters and Derivatives. XXII. Synthesis of 5-Hydroxy-3-pyrrolin-2-ones and 5-Hydroxypyrrolidin-2-ones by Ammonolysis of 5-Methoxyfuran-2(5H)-ones and Derivatives

Francisco Fariña,* M. Victoria Martín, M. Carmen Paredes, M. Carmen Ortega, and Amelia Tito

*Instituto de Química Orgánica General, C. S. I. C., Calle Juan de Cierva, 3, 28006 Madrid, Spain

Abstract

The ammonolysis of 4-substituted 5-methoxyfuran-2(5H)-ones 4a-e under mild conditions affords the respective 5-hydroxy-3-pyrrolin -2-ones 5a-e. However, 4-dialkylamino derivatives 4f,g do not react with ammonia under the same conditions. Similar ammonolysis of furanone derivatives 7a,b,10 and 13 yields the pyrrolidinones 8a,b and hexahydroisoindolones 11, and 14, respectively. The corresponding methoxylactams 6a-e, 9a-b and 12 are readily obtained by refluxing the hydroxylactams 5a-e, 8a,b and 11, respectively with acid-catalyzed methanol.