Palladium-catalysed Heteroannulation with Acetylenic Carbinols: Synthesis of 3-Acylmethylisoindolin-1-ones

Abstract

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.

References

1. E. Valencia, A. J. Freyer, M. Shamma and V. Fajardo, Tetrahedron Lett., 1984, 25, 599.
2. (a) T. R. Belliotti, W. A. Brink, S. R. Kesten, J. R. Rubin, D. J. Wustrow, K. T. Zoski, S. Z. Whetzel, A. E. Corbin, T. A. Pugsley, T. G. Heffner and L. D. Wise, 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. R. A. Abramovitch, I. Shinkai, B. J. Mavunkel, K. M. More, S. O'Connor, G. H. Ooi, W. T. Pennington, P. C. Srinivasan and J. R. Stowers, Tetrahedron, 1996, 52, 3339.
4. (a) J. S. Mahanty, M. De and N. G. Kundu, 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. M. W. Khan and N. G. Kundu, Synlett, 1997, 1435.
6. (a) E. Dominguez, E. Martinez de Marigorta, L. Carrillo and R. Fananas, 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. N. G. Kundu and M. W. Khan, Tetrahedron Lett., 1997, 38, 6937.
8. X-Ray diffraction data unequivocally established the structures of 3-alkylidene isoindolin-1-ones: M. W. Khan, S. Guha, A. K. Mukherjee and N. G. Kundu, Acta Crystallogr., Sect. C., 1998, 54, 119.