Palladium-catalysed reactions of 2-iodobenzamides 1–6 with acetylenic carbinols 7–12 having a terminal acetylenic group and an adjacent carbinol functionality result in the formation of the 3-acylmethylisoindolin-1-ones 13–23 in one step.
(a) BelliottiT. R., BrinkW. A., KestenS. R., RubinJ. R., WustrowD. J., ZoskiK. T., WhetzelS. Z., CorbinA. E., PugsleyT. A., HeffnerT. G., and WiseL. D., Bioorganic. Med. Chem. Lett., 1998, 8, 1499. (b) Z.-P. Zhuang, M.-P. Kung, M. Mu and H. F. Kung, J. Med. Chem., 1998, 41, 157.
3.
AbramovitchR. A., ShinkaiI., MavunkelB. J., MoreK. M., O'ConnorS., OoiG. H., PenningtonW. T., SrinivasanP. C., and StowersJ. R., Tetrahedron, 1996, 52, 3339.
4.
MahantyJ. S., DeM., and KunduN. G., J. Chem. Soc., Perkin Trans. 1, 1997, 2577; (b) N. G. Kundu, M. Pal, J. S. Mahanty and M. De, J. Chem. Soc., Perkin Trans. 1, 1997, 2815; (c) J. S. Mahanty, M. De, P. Das and N. G. Kundu, Tetrahedron, 1997, 53, 13397; (d) C. Chowdhury, G. Chaudhuri, S. Guha, A. K. Mukherjee and N. G. Kundu, J. Org. Chem., 1998, 63, 1863.
5.
KhanM. W., and KunduN. G., Synlett, 1997, 1435.
6.
(a) DominguezE., Martinez de MarigortaE., CarrilloL., and FananasR., Tetrahedron, 1991, 47, 9253; (b) A. Couture, H. Cornet and P. Grandclaudon, Tetrahedron, 1992, 48, 3857; (c) A. Sugimoto, H. Shinba-Tanaka and M. Ishikawa, Synthesis, 1995, 431.
7.
KunduN. G., and KhanM. W., Tetrahedron Lett., 1997, 38, 6937.
8.
X-Ray diffraction data unequivocally established the structures of 3-alkylidene isoindolin-1-ones:KhanM. W., GuhaS., MukherjeeA. K., and KunduN. G., Acta Crystallogr., Sect. C, 1998, 54, 119.
