A new multicomponent reaction of nitro compounds with isocyanides

Abstract

The first multicomponent reaction between nitro compounds, isocyanides and acylating agents is described, providing an original route to α-oximinoamides.

References

1. D. T. W. Chu, Annual Reports in Medical Chemistry Vol 33, ed. J. A. Bristol, Academic Press, San Diego, 1998, pp. 141–150.
2. C. Buron, L. El Kaïm and A. Uslu, Tetrahedron Lett., 1997, 38, 8027; L. El Kaïm and E. Pinot-Périgord, Tetrahedron, 1998, 54, 3799.
3. E. Breuer, The Chemistry of Amino, Nitroso and Nitro Compounds and their derivatives, ed. S. Patai, Wiley, New York, 1982.
4. H. W. Pinnick, The Nef Reaction, Organic Reaction Vol 38, ed. L. A. Paquette, Wiley, 1990, p. 659.
5. K. B. G. Torsell, Nitrile Oxides, Nitrones, and Nitronates in Organic Synthesis, VCH, Weinheim, 1988; M. Cherest and X. Lusinchi, Tetrahedron, 1986, 42, 3825.
6. A. McKillop and R. J. Kobylecki, Tetrahedron, 1974, 30, 1365.
7. E. W. Colvin, A. D. Robertson, D. Seebach and A. K. Beck, J. Chem. Soc., Chem. Commun., 1981, 952.
8. I. Ugi, Isonitrile Chemistry, Academic Press, New York, 1971.
9. L. El Kaïm and A. Gacon, Tetrahedron Lett., 1997, 38, 3391.
10. T. Fujisawa, Y. Kurita and T. Sato, Chem. Lett., 1993, 1537.
11. A typical experimental procedure is as follows: to a solution of nitro compound (2 mmol) in toluene (2 ml) were added NEt₃(2.2 mmol), acetic anhydride (2.2 mmol) and isocyanide (3 mmol). The reaction was stirred at room temperature under an inert atmosphere until completion (a few hours to a few days for aliphatic nitro compounds); evaporation of the solvent and chromatography on silica finally furnished the desired product.