Abbas Rahmati, Zahra Khalesi

Abstract: A one-pot three component condensation synthesis of imidazo[1,5-a]pyridines using of various aromatic aldehydes and dipyridil ketone with ammonium acetate in the presence of Lithium chloride as catalyst in good yields under microwave irradiation has been described.

Keywords: Lithium Chloride; Imidazo[1, 5-a]pyridine; Microwave Irradiation

Cite this paper: nullA. Rahmati and Z. Khalesi, "One-Pot Three-Component Synthesis of Imidazo[1,5-a]pyridines," International Journal of Organic Chemistry, Vol. 1 No. 2, 2011, pp. 15-19. doi: 10.4236/ijoc.2011.12003.

References

[1]   J. A. Joule, K. Mills, Heterocyclic Chemistry, 4th ed.; Black Science: Oxford, U.K., 2000; Chapter 25.

[2]   J.A. Montgomery, J.A., Secrist, III. In Comprehensive Heterocyclic Chemistry; A.R. Katritzky, C.W. Rees, Eds.; Pergamon Press: Oxford, 1984; Vol. 5, p 614.

[3]   D. Kitazawa, G. Tominaga, A. Takano, Jpn. Kokai Tokkyo Koho JP 2001057292; Chem. Abstr. 134 (2001) 200276.

[4]   H. Nakamura, H. Yamamoto, PCT Int. Appl. WO 2005043630; Chem. Abstr. 142 (2005) 440277.

[5]   Fuentes, W.W. Paudler, J. Org. Chem. 40 (1975) 1210.

[6]   J.D. Bower, G.R. Ramage, J. Chem. Soc. (1955) 2834.

[7]   E. Abushanab, A.P. Bindra, J. Org. Chem. 38 (1973) 2049.

[8]   N.F. Ford, L.J. Browne, T. Campell, C. Gemenden, R.C. Gude, J.W.F. Waley, J. Med. Chem. 28 (1985) 164.

[9]   J. Bourdais, A.-M.E. Omar, J. Heterocycl. Chem. 17 (1980), 555.

[10]   D.J. Hlasta, M. Silbernagel, Heterocycles, 48 (1998) 1015.

[11]   J.A. Montgomery, J.A. Secrist, In Comprehensive Heterocyclic Chemistry; A.R. Katritzky, C.W. Rees, Eds.; Pergamon Press: Oxford, 1984; Vol. 5, p 634.

[12]   P. Blatcher, D. Middlemiss, Tetrahedron Lett. 21 (1980) 2195.

[13]   D. Hlasta, Tetrahedron Lett. 1990, 31, 5833.

[14]   L.J. Browne, C. Gude, H. Rodriguez, R.E. Steele, A. Bhatnager, J. Med. Chem. 34 (1991) 725.

[15]   T. Benincori, E. Brenna, F. Sannicolo, J. Chem. Soc., Perkin Trans. 1 (1993) 675.

[16]   F. Shibahara, A. Kitagawa, E. Yamaguchi, T. Murai Org. Lett. 8 (2006) 5621.

[17]   D. Kim, L. Wang, J.J. Hale, C.L. Lynch, R.J. Budhu, M. MacCoss, S.G. Mills, L. Malkowitz, S.L. Gould, J.A. DeMartino, M.S. Springer, D. Hazuda, M. Miller, J. Kessler, R.C. Hrin, G. Carver, A. Carella, K. Henry, J. Lineberger, W.A. Schleif, E.A. Eminic, Bioorg. Med. Chem. Lett. 15 (2005) 2129.

[18]   M.E. Bluhm, M. Ciesielski, H. G?rls, D?ring, M. Angew. Chem., Int. Ed. 41 (2002) 2962.

[19]   M.E. Bluhm, C. Folli, D. Pufky, M. Kr?ger, O. Walter, M. D?ring, Organometallics 24 (2005) 4139.

[20]   A.P. Krapcho, J.R. Powell, Tetrahedron Lett. 27 (1986) 3713.

[21]   F. Palacios, C. Alonso, G. Rubiales, Tetrahedron 51 (1995) 3683.

[22]   A.R. Katritzky, G. Qiu, J. Org. Chem. 66 (2001) 2862.

[23]   J. Wang, L. Dyers, R. Mason, P. Amoyaw, X.R. Bu, J. Org. Chem. 70 (2005) 2353.

[24]   J. Wang, R. Mason, D. VanDerveer, K. Feng, X.R. Bu, J. Org. Chem. 68 (2003) 5415.

[25]   S.A. Siddiqui, T.M. Potewar, R.J. Lahoti, K.V. Srinivasan, Synthesis (2006) 2849.

[26]   Rahmati, Tetrahedron. Lett. 51 (2010) 2967.