One-pot synthesis of coumarins . Catalysis by the solid base, calcined Mg-Al hydrotalcite

Abstract

The synthesis of coumarins (2H-benzopyran-2-ones) via Knoevenagel condensation over a recoverable, inexpensive solid base catalyst, calcined Mg–Al hydrotalcite, is reported for the first time. This method produces substituted coumarins in very high yields (>85%) and selectivities (ca. 100%) when aromatic hydroxy aldehydes are reacted with 2-substituted ethyl acetate.

References

1. R. A. Sheldon, Chem. Ind., (1) 6th Jan. 1997, p. 12.
2. J. M. Thomas and C. R. Theocharis, in Perspectives in Catalysis, ed. J. M. Thomas and K. I. Zamaraev, Blackwell Scientific Publications, London, 1992, p. 465.
3. C. B. Dartt and M. E. Davis, Catal. Today, 1994, 19, 151.
4. H. Hattori, Chem. Rev., 1995, 95, 537.
5. Y. Ono and T. Baba, Catal. Today, 1997, 38, 321.
6. F. Cavani, F. Trifiro and A. Vaccari, Catal. Today, 1991, 11, 173.
7. M. Lakshmi Kantam, B. M. Choudhary, Ch. Venkata Reddy, K. Koteswara Rao and F. Figueras, Chem. Commun., 1998, 1033.
8. A. Corma, V. Fornés, R. M. Martín-Aranda and F. Sanchéz, J. Catal., 1990, 126, 192; A. Corma, V. Fornés and R. M. Martín-Aranda, Appl. Catal., 1990, 59, 234; A. Corma, V. Fornés, R. M. Martín-Aranda and F. Rey, J. Catal., 1992, 134, 58; M. J. Climent, A. Corma, S. Iborra and J. Primo, J. Catal., 1995, 151, 60.
9. I. Roderiguez, H. Cambon, D. Brunel and M. Laspéras, J. Mol. Catal. A: Chem., 1998, 130, 195.
10. C. H. Schroder and K. P. Link, J. Am. Chem. Soc., 1957, 79, 3291; A. M. A. Drug Evaluations, Publishing Sciences Group Inc., Littleton, MA, 3rd edn., 1977, p. 121.
11. Y. L. Chen, T. C. Wang, S. C. Liang, C. M. Teng and C. C. Tzeng, Chem. Pharm. Bull., 1996, 44, 1591; Y. L. Chen, T. C. Wang, K. H. Lee, C. C. Tzeng and C. M. Teng, Helv. Chem. Acta, 1996, 79, 651.
12. M. H. Elangdi, S. O. Abdallah, K. M. Ghoneim, E. M. Ebied and K. N. Kassab, J. Chem. Res. (S), 1997, 44.
13. A. J. Hoefnagel, E. A. Gunnewegh, R. S. Downing and H. van Bekkum, J. Chem. Soc., Chem. Commun., 1995, 225.
14. D. Tichit, M. H. Lhouty, A. Guida, B. H. Chiche, F. Figueras, A. Auroux, D. Bartalini and E. Garrone, J. Catal., 1995, 151, 50.
15. A. Corma, S. Iborra, J. Primo and F. Rey, Appl. Catal., 1994, 114, 215.
16. Y. V. Subba Rao, D. E. De Vos and P. A. Jacobs, Angew. Chem., 1997, 109, 2776; Angew. Chem., Int. Ed. Engl., 1997, 36, 2661.