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
محورهای موضوعی : 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.
کلید واژه: 1, Ionic Liquid, Aldehydes, Catalyst, 3-dicarbonyl compounds,
چکیده مقاله :
A highly practical and efficient preparation of pyrano[3,2-c]pyridone and pyrano[3,2-c]quinoline derivatives was developed via an ionic liquid mediated and promoted multi-component reaction of malononitrile, aldehyde, and 4-hydroxyquinolin-2(1H)-one or 4-hydroxy-6-methylpyridin-2(1H)-one. The combinatorial syntheses were achieved for the first time without applying extra activation energy at ambient temperature while making use of [BMIm]Cl as a catalyst solvent.
[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.
