[1+4] Cycloaddition of Isocyanides with3-(1-Hydroxyethylidene)pentane-2,4-dione. A Convenient Synthesisof Iminolactones†

Abstract

Isocyanides undergo formal [1+4] cycloaddition with3-(1-hydroxyethylidene)pentane-2,4-dione to afford five-memberediminolactone derivatives in high yields.

References

1. I. Ugi, Angew. Chem., Int. Ed. Engl., 1982, 21, 810.
2. H. M. Walborsky and M. P. Periasamy, in The Chemistry of Functional Groups, Supplement C, ed. S. Patai and Z. Rappoport, Wiley, New York, 1983, ch. 20, pp. 835–887.
3. S. Marcaccini and T. Torroba, Org. Prep. Proced. Int., 1993, 25, 141.
4. James H. Rigby and Maher Qabar, J. Am. Chem. Soc., 1991, 113, 8975.
5. Mark Westling and Tom Livinghouse, J. Am. Chem. Soc., 1987, 109, 590.
6. Dennis P. Curran and Hui Liu, J. Am. Chem. Soc., 1991, 113, 2127.
7. I. Yavari, A. Shaabani and M. T. Maghsoodlou, Monatsh. Chem., 1997, 128, 697.
8. G. Morel, E. Marchand and A. Foucaud, J. Org. Chem., 1990, 55, 1721.
9. D. Moderhack, Synthesis, 1985, 1083.
10. S. Forsen and M. Nilsson, Acta Chem. Scand., 1959, 44, 2997.