A green, efficient, and rapid procedure for the synthesis of pyrano[3,2-c] quinoline and pyrano[3,2-c]pyridone derivatives catalyzed by [BMIm]Cl
Subject Areas : Iranian Journal of CatalysisEsmayeel Abbaspour-Gilandeh 1 , Seyyedeh Cobra Azimi 2 , Kurosh Rad-Moghadam 3 , Aidin Mohammadi-Barkchai 4
1 - Department of Chemistry, Faculty of Science, University of Guilan, Rasht, zip code 41335, I.R. Iran.
2 - Department of Chemistry, Faculty of Science, University of Guilan, Rasht, zip code 41335, I.R. Iran.
3 - Department of Chemistry, Faculty of Science, University of Guilan, Rasht, zip code 41335, I.R. Iran.
4 - Department of Applied chemistry, Ardabil Branch, Islamic Azad University, Ardabil, zip code 56157, I.R. Iran.
Keywords:
Abstract :
[1] A. Strecker, Liebigs Ann. Chem. 75 (1850) 27-51.
[2] J. Zhu, H. Bienaymé, In Multi component Reactions, Wiley-VCH: Weinheim, 2005.
[3] A. Domling, Comb. Chem. High Through put Screen. 1 (1998) 1-22.
[4] H. Bienayme, C. Hulme, G. Oddon, P. Schmitt, Chem-Eur. J. 6 (2000) 3321-3329.
[5] (a) M. A. P. Martins, C.P. Frizzo, D. N. Moreira, N. Zanatta, H. Bonacorso, Chem. Rev. 108 (2008) 2015-2050. (b) J. D. Holbrey, M.B. Turner, W. M. Reichert, R. D. Rogers, Green Chem. 5 (2003) 731-736.
[6] L. A. Aslanov, M.A. Zakharov, N.L. Abramycheva, Ionic liquids among solvents (in Russ.), Moscow State University Publishing House, Moscow, 2005.
[7] (a) A. R. Hajipour, L. Khazdooz, A. E. Ruoho, Catal. Commun. 9 (2008) 89-96. (b) A. Sharifi, M. S. Abaee, M. Mirzaei, R. Salimi, J. Iran. Chem. Soc. 5 (2008) 135-139. c) M. M. Mojtahedi, M. S. Abaee, H. Abbasi, J. Iran. Chem. Soc. 3 (2006) 93-97. (d) M. M. Khodaei, A. R. Khosropour, S. Ghaderi, J. Iran. Chem. Soc. 3 (2006) 69-72. (e) H. Tajik, K. Niknam, F. Parsa, J. Iran. Chem. Soc. 6 (2009) 159-164.
[8] (a) Y. Tang, J. Oppenheimer, Z. Song, L. You, X. Zhang, R. P. Hsung, Tetrahedron. 62 (2006) 10785-10813. (b) T. C. McKee, R. W. Fuller, C.D. Covington, J.H. Cardellina, II, R. J. Gulakowski, B.L. Krepps, J. B. McMahon, M. R. Boyd, J. Nat. Prod. 59 (1996) 754-758. (c) T. C. McKee, C. D. Covington, R. W. Fuller, H. R. Bokesch, S. Young, J. H. Cardellina, II, M. R. Kadushin, D. D. Soejarto, P.F. Stevens, G. M. Cragg, M.R. Boyd, J. Nat. Prod. 61 (1998) 1252-1256. (d) S. J. Wu, I. S. Chen, Phytochemistry. 34 (1993) 1659-1661. (e) E. J. Jung, B. H. Park, Y. R. Lee, Green Chem. 12 (2010) 2003-2011.
[9] (a) S. Kumar, D. Hernandez, B. Hoa, Y. Lee, J. S. Yang, A. McCurdy, Org. Lett. 10 (2008) 3761-3764. (b) M. Rawat, V. Prutyanov, W. D. Wulff, J. Am. Chem. Soc. 128 (2006) 11044-11053. (c) O. A. Fedorova, F. Maure, A. V. Chebunkova, Y. P. Strokach, T. M. Valova, L. G. Kuzmina, J. A. K. Howard, M. Wenzel, K. Gloe, V. Lokshin, A. Samat, J. Phys. Org. Chem. 20 (2007) 469-483. (d) J. D. Hepworth, B. M. Heron, Prog. Heterocycl. Chem. 17 (2005) 33-62.( e) S. Delbaer, J. C. Micheau, G. Vermeersch, J. Org. Chem. 68 (2003) 8968-8973.
[10] C. N. O’Callaghan, T. B. H. McMurry, J. Chem. Res., Synop. (1995) 214-218.
[11] A. H. Adbel-Fattah, A. M. Hesien, S. A. Metwally, M.H. Elnagdi, Liebigs Ann. Chem. (1989) 585-588.
[12] J. M. Quintela, C. Peinador, M. J. Moreira, Tetrahedron 51 (1995) 5901-5912.
[13] S. Srivastava, S. Batra, A. P. Bhaduri, Indian J. Chem., Sect. B. 35B (1996), 602-604.
[14] X. Wang, Z. Zeng, D. Shi, X. Wei, Z. Zong, Synth. Commun. 34 (2004) 3021-3027.
[15] M. Lei, L. Mab, L. Hu, Tetrahedron Lett. 52 (2011) 2597-2600.
[16] (a) I. V. Magedov, M. Manpadi, E. Rozhkova, N. M. Przhevalskii, S. Rogelj, S. T. Shors, W. F. A. Steelant, S. Van Slambrouck, A. Kornienko, Bioorg. Med. Chem. Lett. 17 (2007) 1381-1385. (b) I. V. Magedov, M. Manpadi, M. A. Ogasawara, A. S. Dhawan, S. Rogelj, S. Van slambrouck, W. F. A. Steelant, N. M. Evdokimov, P. Y. Uglinskii, E. M. Elias, E. J. Knee, P. Tongwa, M. Yu. Antipin, A. Kornienko, J. Med. Chem. 51 (2008) 2561-2570. (c) X. Fan, D. Feng, Y. Qu, X. Zhang, J. Wang, P. M. Loiseau, G. Andrei, R. Snoeck, E. Clercq, Bioorg. Med. Chem. Lett. 20 (2010) 809-813.
[17] (a) R. A. Mekheimer, N. H. Mohamed, K. U. Sadek, Bull. Chem. Soc. Jpn. 70 (1997) 1625-1630. b) E. V. Stoyanov, I. C. Ivanov, D. Heber, Molecules 5 (2000) 19-32.
[18] K. Rad-Moghadam, M. Sharifi-Kiasaraie, S. C. Azimi, Tetrahedron 68 (2012) 6472-6476.
[19] K. Rad-Moghadam, S. C. Azimi, J. Mol. Catal. A Chem. 363 (2012) 465-469.
[20] M. Lei, L. Ma, L. Hu, Tetrahedron Lett. 52 (2011) 2597-2600.
