(CTA)3[SiW12]-Li+-MMT: Efficient nanocatalyst for the synthesis of 3,4-dihydropyrimidin-2(1H)-ones under solvent-free conditions
محورهای موضوعی : Iranian Journal of Catalysis
Esmayeel Abbaspour-Gilandeh
1
(Esmayeel Abbaspour-Gilandeh*, Mehraneh Aghaei-Hashjin, Hashem Azizi
Young Researchers and Elites Club, Ardabil Branch, Islamic Azad University, Ardabil, Iran.)
Mehraneh Aghaei-Hashjin
2
(Young Researchers and Elites Club, Ardabil Branch, Islamic Azad University, Ardabil, Iran.)
Hashem Azizi
3
(Young Researchers and Elites Club, Ardabil Branch, Islamic Azad University, Ardabil, Iran.)
کلید واژه: Aldehydes, Multi-component reaction, (CTA)3[SiW12]-Li+-MMT, 3, 4-Dihydropyrimidin-2(1H)-one,
چکیده مقاله :
A highly practical and efficient preparation of 3,4-Dihydropyrimidin-2(1H)-one derivatives was developed via an efficient and simple nanocatalyst and promoted multi-component reaction of ethyl acetoacetate, aromatic aldehyde, and urea in the presence of a catalytic amount of (CTA)3[SiW12]-Li+-MMT under solvent-free conditions. In comparison to the conventional methods, the salient features of this method are green reaction conditions, short reaction time, high quantitative yields, high atom economy, low cost, no column chromatographic separation and easy isolation of products. All the products were characterized by melting point, IR, 1HNMR and 13CNMR and were determined by comparison of their spectra with those of valid samples.
[1] S. Kantevari, S.V.N. Vuppalapati, L. Nagarapu, Catal. Commun. 8 (2007) 1857-1862.
[2] K. Majdzadeh-Ardakani, A.H. Navarchian, F. Sadeghi, Carbohydr. Polym. 79 (2010) 547-554.
[3] B.S. Kumar, A. Dhakshinamoorthy, K. Pitchumani, Catal. Sci. Technol. 4 (2014) 2378-2396.
[4] D.S. Tong, C.H. Zhou, M.Y. Li, W.H. Yu, J. Beltramini, C.X. Lin, Z.P. Xu, Appl. Clay. Sci. 48 (2010) 569-574.
[5] Crystal structures of clay and their X-ray identification, Monograph, ed. G.W. Brindly, G. Brown, Mineralogical Society, London, 1980, pp. 125-195.
[6] E.P. Giannelis, R. Krishnamoorti, E. Manias, Adv. Polym. Sci. 118 (1999) 108-147.
[7] M. Okamoto, S. Mallapragada, B. Narasimhan, Biodegradable Polymer/Layered Silicate Nanocompo-sites: a review, Handbook of Biodegradable Polymeric Materials and Their Applications, American Scientific Publishers, Valencia, California, 2005, pp. 1-45.
[8] S. Yariv, H. Cross, Clays and Clay Minerals, Marcel Dekker, New York, 2002, pp. 463–566.
[9] O. Ozdemir, B. Armagan, M. Turan, M.S. Celik, Dyes Pigm. 62 (2004) 49-60.
[10] H. Shi, T. Lan, T. Pinnavaia, Chem. Mater. 8 (1996) 1584-1587.
[11] S.S. Kim, B.S. Choi, J.H. Lee, K.K. Lee, T.H. Lee, Y.H. Kim, S. Hyunik, Synlett (2009) 599-602.
[12] C.O. Kappe, Eur. J. Med. Chem. 35 (2000) 1043-1052.
[13] K.S. Atwal, B.N.S. Wanson, S.E. Unger, D.M. Floyd, S. Mereland, A. Hedberg, B.C.J. O'Reilly, J. Med. Chem. 34 (1991) 806-811.
[14] P.G. Biginelli, Gazz. Chim. Ital. 23 (1893) 360-413.
[15] U.B. More, Asian J. Chem. 24 (2012) 1906-1908.
[16] J.T. Starcevich, T.J. Laughlin, R.S. Mohan, Tetrahedron Lett. 54 (2013) 983-985.
[17] C.O. Kappe, D. Kumar, R.S. Varma, Synthesis 10 (1999) 1799-1803.
[18] K.A. Kumar, M. Kasthuraiah, C.S. Reddy and C.D. Reddy, Tetrahedron Lett. 42 (2001) 7873-7875.
[19] M.A. Bigdeli, G. Gholami, E. Sheikhhosseini, Chin. Chem. Lett. 22 (2011) 903-906.
[20] F. Tamaddon, Z. Razmi, A.A. Jafari, Tetrahedron Lett. 51 (2010) 1187-1189.
[21] S.D. Salim and K.G. Akamanchi, Catal. Commun. 12 (2011) 1153-1156.
[22] S. Asghari, M. Tajbakhsh, B. Jafarzadeh-Kenari, S. Khaksar, Chin. Chem. Lett, 22 (2011) 127-130.
[23] S. Rostamnia, A. Morsali, RSC Adv. 4 (2014) 10514-10518.
[24] Y. Qiu, H. Sun, Z. Ma, W. Xia, J. Mol. Catal. A: Chem. 392 (2014) 76-82.
[25] E. Abbaspour-Gilandeh, M. Aghaei-Hashjin, A. Yahyazadeh, H. Salemi, RSC Adv. 6 (2016) 55444-55462.
[26] R. Ghosh, S. Maiti, A. Chakraborty, J. Mol. Catal. A: Chem. 217 (2004) 47-50.
[27] Y. Ma, C. Qian, L. Wang, M. Yang, J. Org. Chem. 65 (2000) 3864-3868.
[28] D. Russowsky, F.A. Lopes, V.S.S. Silva, K.F.S. Canto, M.G. Montes, M.N. Godoi, J. Braz. Chem. Soc. 15 (2004) 165-169.
[29] A.D. Patil, N.V. Kumar, W.C. Kokke, M.F. Bean, A.J. Freyer, C.D. Brossi, S. Mai, A. Truneh, D.J. Faulkner, B. Carte, A.L. Breen, R.P. Hertzberg, R.K. Johnson, J.W. Westly, B.C.M. Potts, J. Org. Chem. 60 (1995) 1182-1188.
[30] N.S. Nandurkar, M.J. Bhanushali, M.D. Bhor, B.M. Bhanage, J. Mol. Catal. A: Chem. 271 (2007) 14-17.
[31] J.S. Yadav, B.V.S. Reddy, R. Srinivas, C. Venugopal, T. Ramalingam, Synthesis (2001) 1341-1345.
[32] K.K. Pasunooti, H. Chai, C.N. Jensen, B.K. Gorityala, S. Wang, X.W. Liu, Tetrahedron Lett. 52 (2011) 80-84.
[33] J. Lu, H. Ma, Synlett (2000) 63-64.
[34] P. Salehi, M. Dabiri, M.A. Zolfigol, M.A. Bodaghi Fard, Tetrahedron Lett. 44 (2003) 2889-2891.
[35] M.M. Khodaei, A.R. Khosropour, M. Beygzadeh, Synth. Commun. 34 (2004) 1551-1557.
[36] M. Zeinali-Dastmalbaf, A. Davoodnia, M.M. Heravi, N. Tavakoli-Hoseini, A. Khojastehnezhad, H.A. Zamani, Bull. Korean Chem. Soc. 32 (2011) 656-658.
[37] J. Safaei-Ghomi, R. Tenure, A. Ziarati, Monatsh. Chem. 144 (2013) 1865-1870.
