L-proline catalyzed synthesis of naphthopyranopyrimidines via multicomponent reaction

Document Type: Articles

Author

Young Researchers and Elites Club, Rasht Branch, Islamic Azad University, Rasht, Iran.

Abstract

A green and efficient one pot, three component protocol for synthesis of naphthopyranopyrimidines by cyclocondensation of β-naphthol, aldehyde, and 6-amino-1,3-dimethyluracil using L-proline as a beneficial catalyst with high catalytic activity under solvent-free conditions at 100 °C is described. In this study, several types of aromatic aldehyde, containing electron-withdrawing groups as well as electron-donating groups, were rapidly converted to the corresponding naphthopyranopyrimidine derivatives in good to excellent yields. The present approach offers several advantages such as short reaction times, simple work-up, excellent yields, non-toxicity of the catalyst, and solvent-free conditions.To the best of our knowledge, this is the first report on the synthesis of naphthopyranopyrimidine derivatives using L-proline as a catalyst under solvent-free conditions. The catalysts can be recovered for the subsequent reactions and reused without any loss of efficiency.

Keywords


[1] B.M. Trost, Science 254 (1991) 1471-1477.
[2] A. Domling, I. Ugi, Angew. Chem. Int. Ed. 39 (2000) 3168-3173.
[3] J. Zhu, H. Bienayme, Multicomponent Reactions, Wiley-VCH, Weinheim, 2005.
[4] A. Domling, Chem. Rev. 106 (2006) 17-23.
[5] I. Ugi, Pure Appl. Chem. 73 (2001) 187-191.
[6] R.R. Nagawade, D. B. Shinde, Acta Chim. Slov. 54 (2007) 642-645.
[7] D.M.D’Souza, T. J. Mueller, Chem. Soc. Rev. 36 (2007) 3169-3173.
[8] C.C.A. Cariou, G.J. Clarkson, M. Shipman, J. Org. Chem. 73 (2008) 9762-9764.
[9] (a) C. Kalinski, H. Lemoine, J. Schmidt, C. Burdack, J. Kolb, M. Umkehrer, G. Ross, Synlett (2008) 4007-4011. (b) R.V.A. Orru, M. De Greef, Synthesis (2003) 1471-1499.
[10] (a) Z. Tavakoli, E. Ghasemi, I. Yavari, Iran. J. Catal. 4 (2014) 71-75. (b) A. Khazaei, M.A. Zolfigol, T. Faal-Rastegar, G. Chehardoli, S. Mallakpour, Iran. J. Catal. 3 (2013) 211-220. (c) F. Shirini, G.H. Imanzadeh, M. Abedini, P. Ghods Ghasemabadi, Iran. J. Catal. 3 (2013) 57-65 (d) F. Shirini, G. H. Imanzadeh, M. Abedini, M. Akberi Dokhte-Ghaziania, P. Ghods Ghasemabadi, M. Safarpoor Langroodi, Iran. J. Catal. 2 (2012) 115-119. (e) J. Safaei Ghomi, R. Masoomi, RSC Adv. 4 (2014) 2954-2960. (f) J. Safaei Ghomi, R. Teymuri, A. Ziarati, Monatsh. Chem. 144 (2013) 1865-1870. (g) J. Safaei Ghomi, M. Kiani, A. Ziarati, H. Shahbazi-Alavi, J. Sulfur Chem. 35 (2014), 450-457.
[11] P.T. Anastas, J.C. Warner, Green Chemistry: Theory and Practice; Oxford University Press: New York, p.30, 1998.
[12] E.M. Grivsky, S. Lee, C.W. Sigel, D.S. Duch, C.A. Nichol, J. Med. Chem. 23 (1980) 327-329.
[13] A.H. Bedair, N.A. El-Hady, M.S.A. El-Latif, A.H. Fakery, A.M. El-Arody, Farmaco 55 (2000) 708-714.
[14] D. Heber, C. Heers, U. Ravens, Pharmazie 48 (1993) 537-541.
[15] S.C. Kuo, L.J. Huang, H. Nakamura, J. Med. Chem., 27 (1984) 539-544.
[16] A.M. El-Agrody, M.S. Abd El-Latif, N.A. El-Hady, A. H. Fakery, A.H. Bedair, Molecules 6 (2001) 519-527.
[17] C. Paneda, S. Huitron-Resendiz, L.M. Frago, J.A. Chowen, R. Picetti, L. deLecea, A.J. Roberts, J. Neurosci. 29 (2009) 4155-4161.
[18] M. Radi, S. Schenone, M. Botta, Org. Biomol. Chem. 7 (2009) 2841-2847.
[19] A.H. Bedair, H.A. Emam, N.A. El-Hady, K.A.R. Ahmed, A.M. El-Agrody, Farmaco, 56 (2001) 965-973.
[20] J. Marugan, K. Liu, W. Zheng, R. Eskay, N. Southall, M. Heilig, J. Inglese, C. Austin Probe Reports from the NIH Molecular Libraries Program, Assigned Assay Grant X01-Da026210-01.
[21] G.C. Nandi, S. Samai, M.S. Singh, Synlett 7 (2010) 1133-1137.
[22] S.S. Jalde, V.D. Dhakane, H.V. Chavan, L.K. Adsul, B.P. Bandgar, Synth. React. Inorg. Met.-Org. Nano-Met. Chem. 44 (2014) 623-626.
[23] J.M. Khurana, A. Lumb, A. Chaudhary, B. Nand, RSC Adv. 3 (2013) 1844-1854.
[24] K.P. Kumar, S. Satyanarayana, P.L. Reddy, G. Narasimhulu, N. Ravirala , B.V.S. Reddy, Tetrahedron Lett. 53 (2012) 1738-1741.
[25] G.C. Nandi, S. Samai, R. Kumar, M.S. Singh, Tetrahedron 65 (2009) 7129-7134.
[26] (a) H. Steinhagen, G. Helmchen, Angew. Chem. Int. Ed. Engl. 35 (1996) 2339-2342. (b) M. Shibasaki, Enantiomer 4 (1999) 513-527. (c) N.G. Kozlov, K.N. Gusak, A.B. Tereshko, S.I. Firgangand, A.S. Shashkov. Org. Khim. 40 (2004) 1228-1233.
[27] (a) D.E. Siyutkin, A.S. Kucherenko, M.I. Struchkova, Tetrahedron Lett. 49 (2008) 1212-1216. (b) Armando Cordova, Tetrahedron Lett. 45 (2004) 3949-3952. (c) T. P. Loh, L.C. Feng, Hai-Yan Yang, J.Y. Yang, Tetrahedron Lett. 43 (2002) 8741-8743.
[28] N. Kumaragurubaran, K. Juhl, W. Zhuang, A. Bqgevig, K. Anker Jqrgensen, J. Am. Chem. Soc. 124 (2002) 6254-6255.
[29] H. Shirakawa, Tetrahedron Lett. 55 (2014) 4095-4097.
[30] (a) S.S.P. Kumar Darsi, K. Shiva Kumar, B. Rama Devi, A. Naidu, P.K. Dubey, Lett. Org. Chem. 11 (2014) 551-555. (b) D. Srikrishna, S. Tasqeeruddin, P. Kumar Dubey, Lett. Org. Chem. 11 (2014) 556-563.
[31] (a) M. Dabiri, S.C. Azimi, H.R. Khavasi, A. Bazgir, Tetrahedron 64 (2008) 7307-7311. (b) M. Dabiri, S.C. Azimi, H. R. Khavasi, A. Bazgir, Monatsh. Chem. 138 (2007) 659-661. (c) K. Rad-Moghadam, S.C. Azimi, Tetrahedron 68 (2012) 9706-9712. (d) K. Rad-Moghadam, S.C. Azimi, E. Abbaspour-Gilandeh, Tetrahedron Lett. 54 (2013) 4633-4636. (e) K. Rad-Moghadam, M. Sharifi-Kiasaraie, S.C. Azimi, Tetrahedron 68 (2012) 6472-6476 (f) K. Rad-Moghadam, S.C. Azimi, J. Mol. Catal. A: Chem. 363 (2012) 465-469. (g) A. Bazgir, S.C. Azimi, Iran. J. Catal. 3 (2013) 21-26. (h) S.C. Azimi, H. Kefayati, Iran. J. Catal. 3 (2013) 123-128.