An efficient and general procedure for room-temperature synthesis of benzofurans under solvent-free conditions using KF/Al2O3

Journal of the Iranian Chemical Society

Volumn 5, Issue SUPPL.1, 2008, Pages

  Sharifi, A ^a   Abaee, M S ^a   Tavakkoli, A ^a   Mirzaei, M ^a  

^a CHEMISTRY AND CHEMICAL ENGINEERING RESEARCH CENTER OF IRAN   (Iran)

Author keywords

Benzofuran; KF Al2O3; Rap Stoermer reaction; Solvent free

Indexed keywords

EID: 53349145900     PISSN: 1735207X     EISSN: 17352428     Source Type: Journal    
DOI: 10.1007/bf03246499     Document Type: Article

References (57)

1. a) T.J. Simpson, in: R.H. Thomson (Ed.), The Chemistry of Natural Products, Blackie, London, 1985;
2. b) F.M. Dean, in: J. Apsimon (Ed.), The Total Synthesis of Natural Products, Wiley, New York, vol. 1 (1973) 513.
3. a) A.R. Katritzky, Y. Ji, Y. Fang, I. Prakash, J. Org. Chem. 66 (2001) 5613;
4. b) K.K. Park, H. Seo, J.-G. Kim, I.-H. Suh, Tetrahedron Lett. 41 (2000) 1393;
5. c) K.C. Nicolaou, S.A. Snyder, A. Bigot, J.A. Pfefferkon, Angew. Chem. Int. Ed. 39 (2000) 1093;
6. d) K.K. Park, I.K. Han, J.W. Park, J. Org. Chem. 66 (2001) 6800;
7. e) A. Shafiee, E. Behnam, J. Heterocycl. Chem. 15 (1978) 589.
8. N. Buu-Hoi, G. Saint-Ruf, T.B. Loc, N.D. Xuong, J. Chem. Soc. (1957) 2593.
9. a) K. Benkli, N. Gundogdu-Karaburun, A.C. Karaburun, U. Ucucu, S. Demirayak, N. Kiraz, Arch. Pharm. Res. 26 (2003) 202;
10. b) N. Gundogdu-Karaburun, K. Benkli, Y. Tunali, U. Ucucu, S. Demirayak, Eur. J. Med. Chem. 41 (2006) 651.
11. P.G. Baraldi, R. Romagnoli, I. Beria, P. Cozzi, C. Geroni, N. Mongelli, N. Bianchi, C. Mischiati, R. Gambari, J. Med. Chem. 43 (2000) 2675.
12. a) J. Li, T.S. Rush, III, W. Li, D. De Vincentis, X. Du, Y. Hu, J.R. Thomason, J.S. Xiang, J.S. Skotnicki, S. Tam, K.M. Cunningham, P.S. Chockalingam, E.A. Morris, J.I. Levin, Bioorg. Med. Chem. Lett. 15 (2005) 4961;
13. b) V. Pestellini, A. Giolitti, F. Pasqui, L. Abelli, C. Cutrufo, G. De Salvia, S. Evangelista, A. Meli, Eur. Med. Chem. 23 (1988) 203.
14. A.Y. Leung, S. Foster, Encyclopedia of Common Natural Ingredients Used in Food, Drugs, and Cosmetics, Wiley, New York, 1996.
15. th ed., Vol A18, VCH, Weinheim (1999) 153.
16. a) S. Thielges, E. Meddah, P. Bisseret, J. Eustache, Tetrahedron Lett. 45 (2004) 907;
17. b) M.V. Gil, E. Roman, J.A. Serrano, Tetrahedron Lett. 41 (2000) 10201;
18. c) J.W. Herndon, Y. Zhang, H. Wang, K. Wang, Tetrahedron Lett. 41 (2000) 8687;
19. d) A. Arrault, F. Touzeau, G. Guillaument, J.Y. Merour. Synthesis (1999) 1241.
20. a) D.D. Hennings, S. Iwasa, V.H. Rawal, Tetrahedron Lett. 36 (1997) 6379;
21. b) X. Xie, B. Chen, J. Lu, J. Han, X. She, X. Pan, Tetrahedron Lett. 45 (2004) 6235;
22. c) S.W. Youn, J.I. Eom, Org. Lett. 7 (2005) 3355.
23. a) D. Bogdal, M. Warzala, Tetrahedron 56 (2000) 8769;
24. b) K.K. Park, J. Jeong. Tetrahedron 61 (2005) 545;
25. c) E. Bellur, I. Freifeld, P. Langer, Tetrahedron Lett. 46 (2005) 2185;
26. d) D. Bogdal, S. Bednarz, M. Lukasiewicz, Tetrahedron 62 (2006) 9440;
27. e) G.A. Kraus, N. Zhang, J.G. Verkade, M. Nagarajan, P.B. Kisanga, Org. Lett. 2 (2000) 2409;
28. f) M.C. Cruz, J. Tamariz, Tetrahedron Lett. 45 (2004) 2377.
29. W.M. Dai, K.W. Lai, Tetrahedron Lett. 43 (2002) 9377;
30. b) C.G. Bates, P. Saejueng, J.M. Murphy, D. Venkataraman, Org. Lett. 4: (2002) 4727.
31. a) E. Rap, Gazz. Chim. Ital. 285 (1895) 2511;
32. b) R. Stoermer, Liebigs. Ann. Chem. 312 (1900) 331.
33. M.L.N. Rao, D.K. Awasthi, D. Banerjee, Tetrahedron Lett. 48 (2007) 431.
34. K. Yoshizawa, S. Toyota, F. Toda, I. Csoregh, Green Chem. 5 (2003) 353.
35. J. Habermann, S.V. Ley, R. Smits. J. Chem. Soc., Perkin Trans. 1 (1999) 2421.
36. R.S. Varma, D. Kumar, P.J. Liesen, J. Chem. Soc., Perkin Trans. 1 (1998) 4093.
37. B.E. Blass, Tetrahedron, 58 (2002) 9301.
38. W.C. Wong, D. Wang, C. Forray, P.J.J. Vaysse, T.A. Branchek, C. Gluchowski, Bioorg. Med. Chem. Lett. 4 (1994) 2317.
39. V.K Yadav, K.K. Kapoor, Tetrahedron 52 (1996) 3659.
40. J. Yamawaki, T. Ando, Chem. Lett. (1980) 533
41. J. Yamawaki, T. Ando, T. Hanafusa, Chem. Lett. (1981) 1143.
42. F. Polyak, T. Dorofeeva, R. Sturkovich, Y. Goldberg, Synth. Commun. 21 (1991) 239.
43. Q.S. Hu, C.M. Hu, Chin. Chem. Lett. 8 (1997) 665.
44. H.M.S. Kumar, B.V.S. Reddy, E.J. Reddy, J.S. Yadav, Green Chem. 1 (1999) 141.
45. J. Yamawaki, T. Kawate, T. Ando, T. Hanafusa, Bull. Chem. Soc. Jpn. 56 (1983) 1885.
46. A.K.S.B. Rao, C.G. Rao & D.B. Singh, Synth. Commun. 21 (1991) 443.
47. F. Berree, E. Marchand, G. Morel. Tetrahedron Lett. 33 (1992) 6155.
48. B. Peschke, J.G. Bundgaard, J. Breinholt, Tetrahedron Lett. 42 (2001) 5127.
49. a) A. Sharifi, M. Mirzaei, M.R. Naimi-Jamal, J. Chem. Res. (2002) 628;
50. b) A. Sharifi, M. Mirzaei, M.R. Saidi, Tetrahedron Lett. 40 (1999) 1179;
51. c) A. Sharifi, M. Mirzaei, M.R. Naimi-Jamal, Monatsh. Chem. 137 (2006) 213;
52. d) A. Sharifi, M. Mirzaei, M.R. Naimi-Jamal, Synth. Commun. 35 (2005) 1039;
53. e) A. Sharifi, R. Salimi, M. Mirzaei, M.S. Abaee, Synth. Commun. 37 (2007) 1825.
54. L.A. Paquette, Encyclopedia of Reagents for Organic Synthesis, Vol 6, John Wiley & Sons, Chichester (1995) 4223.
55. a) L. Capuano, A. Ahlhelm, H. Hartmann, Chem. Ber. 119 (1986) 2069;
56. b) G. Litkei, K. Gulacsi, S. Antus, Z. Dinya, Synth. Commun. 26 (1996) 3061;
57. c) V.G.S. Box, P.C. Meleties, Tetrahedron Lett. 39 (1998) 7059.