1,3-Dipolar cycloaddition of nitrilimines to a variety of 2-arylmethylidene-1-indanones 1 or 2-arylmethylidene-1,3-indandiones 5 gave the corresponding spiro[2H-indene-2,3′-[3H]pyrazol]-1(3H)-one 3 and their 1,3-dione derivatives 6 in high regioselectivity. The stereo-configuration of 3 (3'R, 4'S or its enantiomeric form) was established by nOe-difference technique as well as single crystal X-ray diffraction analysis.
References
1.
PadwaA., 1,3-Dipolar Cycloaddition Chemistry, John-Wiley & Sons, Inc., New York, 1984, vol. 1, p. 291.
2.
NagaseS., and YoshidaZ., J. Org. Chem., 1995, 60, 5372.
3.
MuthuS., MaruthamuthuP., RagunathanR., RaoP. R., and VasudevaM. C. K., Tetrahedron Lett., 1994, 35, 1763.
4.
AnelliP.L., and CroceP. D., Gazz. Chim. Ital., 1981, 111, 269.
5.
HassaneenH.M., HilalR. H., ElwanN. M., HarhashA., and ShawaliA. S., J. Heterocycl. Chem., 1984, 21, 1013.
6.
AbdallahM.A., AlbarH. A., and ShawaliA. S., J. Chem. Res. (S), 1993, 182.
7.
FathiT., CiamalaK., Dinh AnN., and VebrelJ., Can. J. Chem., 1994, 72, 1424.
