Vinyltriphenylphosphonium Salt-mediated New Synthesis of Functionalized Maleimides

Abstract

N-Methyl-2-chloroacetoacetamide undergoes a complex reaction with dialkyl acetylenedicarboxylates and triphenylphosphine to produce dialkyl 2-(N-methyl-2-chloroacetoacetamide-2-yl)-3-(triphenylphosphoranylidene)-butanedioates, which undergo elimination-cyclization reactions to produce N-methyl-4-acetyl-3-(alkoxycarbonyltriphenylphosphoranylidene)-maleimides.

References

1. P. Laszlo, Organic Reactions: Simplicity and Logic, Wiley, New York, 1995.
2. B. C. Hamper, D. R. Dukesherer and M. S. South, Tetrahedron Lett., 1996, 37, 3671.
3. T. Iijima, N. Suzuki, W. Fukuda and M. Tomoi, J. Eur. Polym., 1995, 31, 775.
4. P. Y. Reddy, S. Kondo, T. Toru and Y. Ueno, J. Org. Chem., 1997, 62, 2652.
5. D. E. C. Corbridge, Phosphorus. An Outline of the Chemistry, Biochemistry and Uses, Elsevier, Amsterdam, 5th edu., 1995; R. Engel, Synthesis of Carbon–Phosphorus Bonds, CRC Press, Boca Raton, FL, 1988.
6. O. I. Kolodiazhnyi, Russ. Chem. Rev., 1997, 66, 225.