Preparation of 1,5-diaryl-3-(arylamino)-1H-pyrrol- 2(5H)-one derivatives using 1-methylpiperidinium hydrogen sulfate as an efficient catalyst
محورهای موضوعی : Journal of the Iranian Chemical ResearchMajid Ghashang 1 , Mohammad Reza Mohammad Shafiee 2 , Batool Hojati Najafabadi 3
1 - Department of Chemistry, Faculty of Sciences, Najafabad Branch, Islamic Azad University,
Najafabad, Esfahan, Iran
2 - Department of Chemistry, Faculty of Sciences, Najafabad Branch, Islamic Azad University,
Najafabad, Esfahan, Iran
3 - Department of Chemistry, Faculty of Sciences, Najafabad Branch, Islamic Azad University,
Najafabad, Esfahan, Iran
کلید واژه: Ionic liquid, 1, 5-diaryl-3-(arylamino)-1H-pyrrol-2(5H)-one, γ-lactam, 1-methylpiperidinium hydrogen sulfate,
چکیده مقاله :
A highly efficient and environmentally friendly synthesis of various 1,5-diaryl-3-(arylamino)-1H-pyrrol-2(5H)-ones catalyzed by 1-methylpiperidinium hydrogen sulfate via one-pot cyclo-condensation reaction ofaldehydes, amines and ethyl 2-oxopropanoate under ambient conditions has been explored. The presentmethodology offers several advantages such as good yields, simple procedure, shorter reaction times andmilder conditions and the products were purified without resorting to chromatography.
[1] J. Zhu, H. Bienaymi, (Eds.) Multicomponent Reactions, Wiley-VCH, Weinheim, 2005.
[2] A. Dömling, I. Ugi, Angew. Chem. Int. Ed. 39 (2000) 3168-3210.
[3] S. Maiti, S. Biswas, U. Jana, J. Org. Chem. 75 (2010) 1674-1683.
[4] R.B. Morin, M. Gorman, Chemistry and Biology of β-Lactam Antibiotics; Academic Press, New York,
1982.
[5] R.D. Miller, P. Goelitz, J. Org. Chem. 46 (1981) 1616-1618.
[6] M.A. Ogliaruso, J.F. Wolfe, In: Synthesis of Lactones and Lactams. S Patai, Z Rappoport, editors. John
Wiley & Sons; New York, 1993.
[7] N.R. Candeias, P.M.P. Gois, C.A.M. Afonso, J. Org. Chem. 71 (2006) 5489-5497.
M.R.M. Shafiee et al., J. Iranian Chem. Res. 5 (2) (2012) 65-71
71
[8] A.E. Taggi, A.M. Hafez, H. Wack, B. Young, D. Ferraris, T. Lectka, J. Am. Chem. Soc. 124 (2002)
6626-6635.
[9] R.B. Lettan, C.V. Galliford, C.C. Woodward, K.A. Scheidt, J. Am. Chem. Soc. 131 (2009) 8805-8814.
[10] S.T. Kocharyan, N.P. Churkina, T.L. Razina, V.E. Karapetyan, S.M. Ogandzhanyan, V.S. Voskanyan,
A.T. Babayan, Khim. Geterotsikl. Soedin. (1994) 1345-1350.
[11] Y.C. Wu, L. Liu, D. Wang, Y.J. Chen, J. Heterocycl. Chem. 43 (2006) 949-955.
[12] F. Palacios, J. Vicario, D. Aparicio, Eur. J. Org. Chem. (2006) 2843-2850.
[13] X. Li, H. Deng, S. Luo, J.-P. Cheng, Eur. J. Org. Chem. (2008) 4350-4356.
[14] M.R. Mohammad Shafiee, B. Hojati Najafabadi, M. Ghashang, J. Chem. Res. 35 (2011) 634-636.
[15] P. Wasserscheid, W. Keim, Angew. Chem. Int. Ed. Engl. 39 (2000) 3772-3789.
[16] C. Xie, H. Li, L. Li, S. Yu, F. Liu, J. Hazard. Mater. 151 (2008) 847-850.
[17] F. Chavez, S. Subrez, M.A. Diaz, Synth. Commun. 24 (1994) 2325-2339.
[18] D.M. Tal, E. Einan, Y. Mazur, Tetrahedron 37 (1981) 4327-4330.
[19] F. d’Yvoire, Bull. Soc. Chim. Fr. (1961) 2277, pdf file no.00-014-0546.
[20] A.K. Chakraborti, R. Gulhane, Chem. Commun. (2003) 1896-1897.