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Paper | Special issue | Vol 52, No. 1, 2000, pp.237-251
Published online, 1st January, 1970
DOI: 10.3987/COM-99-S15
Pseudoesters and Derivatives. Part 38. 1,3-Dipolar Cycloadditions of Aryl Azides and an Aziridine, via Azomethine Ylide, to 2(5H)-Furanones Substituted at the 5-Position by Methoxy and Sulfur Bearing Group

Gemma Gonzalez, M. Victoria Martín, and M. Carmen Paredes*

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

Abstract

The behavior of the 2(5H)-furanones (1-3) towards p-methoxy- and p-nitrophenyl azides (4 and 12) has been investigated, in particular with respect to the regio- and stereoselectivity. The 1,3-dipolar cycloaddition of the azometbine ylide generated by thermal ring opening of dimethyl trans-1-(p-methoxyphenyl)aziridine-2,3-dicarboxylate (22) to 2(5H)-furanones (1-3) proceeds in good yield and affords functionalized furo[3,4-c]pyrrol-3-one derivatives.