ZrCl4 catalysed solvent free synthesis of coumarins

Journal of Chemical Research

Volumn , Issue 7, 2004, Pages 480-481

  Gangadasu, B ^a   Narender, P ^a   Raju, B China ^a   Rao, V Jayathirtha ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

Coumarins; Pechmann reaction; Solvent free conditions; Synthesis; Zirconium tetrachloride

Indexed keywords

EID: 22144456836     PISSN: 03082342     EISSN: None     Source Type: Journal    
DOI: 10.3184/0308234042037194     Document Type: Article

References (42)

1. R.O. Kennedy and R.D. Thornes, Coumarins: Biology, Application and Mode of Action; Wiley & Sons; Chichester, 1997.
2. L.A. Singer and N.P. Kong, J. Am. Chem. Soc., 1996, 88, 5213.
3. M. Zahradnik, The Production and Application of Fluorescent Brightening Agents, Wiley & Sons, Chichester 1992.
4. R.D.H. Murray, J. Mendez and S.A. Brown, The Natural Coumarins: Occurrence Chemistry and Biochemistry; Wiley & Sons, New York, 1982.
5. (a) H. Pechmann and C. Duisberg, Chem. Ber., 1884, 17, 929;
6. J.R. Jonson, Org. React. 1942, 1, 210;
7. G. Jones, Org. React., 1967, 15, 204;
8. G. Brufola, F. Fringuelli, O. Piermatti and F. Pizzo, Heterocycles, 1996, 43, 1257;
9. R.L. Shriner, Org. React., 1942, 1, 1.
10. (a) N.S. Narasimhan, R.S. Mali and M.V. Barve, Synthesis, 1979, 906;
11. I. Yavari, R. Hekmatshoar and A. Zonouzi, Tetrahedron Lett., 1998, 39, 2391.
12. (a) H. Appel, J. Chem. Soc., 1935, 1031;
13. L.L. Woods and J. Sapp, J. Org. Chem., 1962, 27, 3703;
14. Z.S. Ahmad and R.D. Desai, Proc. Indian. Acad. Sci., 1937, 5A, 277;
15. Chem. Abstr., 1937, 31, 5785;
16. R. Robinson and F. Weygand, J. Chem. Soc., 1941, 386;
17. S.M. Sethna, N.M. Shah and R.C. Shah, J. Chem. Soc., 1938, 228.
18. D.S. Bose, A.P. Rudra Das and M. Haribabu, Tetrahedron Lett., 2002, 43, 9195.
19. S.P. Chavan, K. Shivasankar, R. Sivappa and R. Kale, Tetrahedron Lett., 2002, 43, 8583.
20. (a) M.K. Potdar, S.S. Mohile and M.M. Salunkhe, Tetrahedron Lett., 2001, 42, 9285;
21. A.C. Khandekar and B.M. Khadilkar, Synlett, 2002, 152.
22. (a) E.V.O. John and S.S. Israelstam, J. Org. Chem., 1961, 26, 240;
23. D.A. Chaudhari, Chem. Ind., 1983, 568;
24. A.J. Hoefnagel, E.A. Gunnewegh, R.S. Downing and H. Vanbekkum, J. Chem. Soc., Chem. Commun., 1995, 225.
25. (a) A. De la Hoz, A. Moreno and E. Vazquez, Synlett, 1999, 608;
26. S. Frere, V. Thiery and T. Besson, Tetrahedron Lett., 2001, 42, 2791.
27. (a) J.E. Huheey, Inorganic Chemistry, 3rd edn.; Roger & Harper Row: Singapore, 1990, Chapter 18;
28. LD50 (Oral, rat) of ZrCl4 is 1688 mg kg-1 [Emsley, J. The Elements; 3rd edn. Clarendon: Oxford, 1988];
29. P. J. Moles, http://www.zrchem.com
30. (a) G.V.M. Sharma, Ch. Govardhan Reddy and P. Radha Krishna, Synlett, 2003, 11, 1728;
31. G.V.M. Sharma, Ch. Govardhan Reddy and P. Radha Krishna, J. Org. Chem., 2003, 68, 4574;
32. Ch. V. Reddy, M. Mahesh, P.V.K. Raju, T.R. Babu and V.V.N. Reddy, Tetrahedron Lett., 2002, 43, 2657.
33. (a) S. Palaniappan, P. Narender, C. Saravanan and V. Jayathirtha Rao, Synlett, 2003, 1793;
34. D. Ravi, N. Rama Rao, G.S.R. Reddy, K. Sucheta and V. Jayathirtha Rao, Synlett, 1994, 856;
35. B. Gangadasu, B. China Raju and V. Jayathirtha Rao, US Pat. 2002, 6,479,664;
36. B. China Raju and V. Jayathirtha Rao, US Pat. 2003, 6,566,528;
37. B. Gangadasu, B. China Raju and V. Jayathirtha Rao, Heterocyclic Commun, 2002, 8, 243.
38. R.S. Mali, Priya P. Joshi, P.K. Sandhu, and Anita Manker. Tilve, J. Chem. Soc., Perkin Trans I, 2002, 371.
39. Antonio de la Hoz, Andres Moreno and Ester Vazquez, Synlett, 1999, 5, 608
40. (a) T. Manimaran, T.K. Thiruvengadam and V.T. Ramakrishan, Synthesis, 1975, 739;
41. L. Crombe and R. Ponsford, J. Chem. Soc (C), 1971, 788.
42. Typical experimental procedure for compounds: A mixture of 4-methoxynaphthol (10 mmol) and ethyl acetoacetate (10 mmol) was stirred at room temperature in the presence of ZrCl4 (10 mol%) for 20 min with a guard tube. After completion of the reaction (TLC), the crude product was subjected to column chromatography to give 6-methoxy-4-methyl-2H-benzo [h] chromene-2-one (5) in 98% yield as colourless crystals, m.p. 134-136°C. 1H NMR (CDCl3, 200 MHz): 2.52 (s, 3H, CH3), 4.06 (s, 3H, OCH3), 6.36 (s, 1H), 6.74 (s, 1H, aromatic), 7.58-7.68 (m, 2H, aromatic), 8.20-8.22 (m, 1H, aromatic), 8.52-8.58 (m, 1H, aromatic). Mass (m/z): 240 (M+), 226, 198, 142, 115, 76 and 39. The other compounds were prepared in a similar manner.