Oxalic acid dihydrate catalyzed synthesis of 3,4-dihydropyrimidin-2-(1H)-one derivatives under thermal and solvent-free conditions

Document Type: Articles

Authors

1 Department of Chemistry, Faculty of Science, University of Sistan and Baluchestan, P. O. Box 98135-674 Zahedan, Iran.

2 Faculty of Science, Velayat University, Iranshahr, Iran.

Abstract

Oxalic acid dihydrate as a green, mild and efficient catalyst for the one-pot three-component Biginelli synthesis of
3,4-dihydropyrimidin-2-(1H)-one derivatives from the reaction between β-keto esters (methyl or ethyl acetoacetate), aromatic aldehyde (benzaldehye derivatives) and urea or thiourea under thermal and solvent-free conditions with excellent yields and short reaction time is studied. The most remarkable benefits of this synthetic method include the green methodology, an eco-friendly, inexpensive and non-toxic catalyst, solvent-free conditions, the availability of materials, and a simple operational procedure with no column chromatographic separation. The products were characterized by melting points, IR and 1H NMR spectroscopy.

Keywords


[1] A. Strecker, Leibigs. Ann. Chem. 75 (1850) 27-45.
[2] M. Abaszadeh, M. Seifib, M. Ghashang. Iran. J. Catal. 5 (2014) 113-117.
[3] N. Hazeri, M.T. Maghsoodlou, S. Mohamadian Souri, M. Lashkari, M. Ghashang, Iran. J. Catal. 5 (2015) 9-14.
[4] L. Moradi, G.R. Najafi, H. Saeidiroshan. Iran. J. Catal. 5 (2015) 357-364.
[5] H. Eshghi, M. Rahimizadeh, S.M. Mousavi. Iran. J. Catal. 4 (2014) 235-239.
[6] S.S. Sajadikhah, M.T. Maghsoodlou, N. Hazeri, Chin. Chem. Lett. 25 (2014) 58-60.
[7] S.S. Sajadikhah , N. Hazeri, M.T. Maghsoodlou, S.M. Habibi-Khorassani, Kh. Khandan-Barani, J. Chem. Res. 37 (2013) 40-42.
[8] Z. Madanifar, M.T. Maghsoodlou, M. Kangani, N. Hazeri, Res. Chem. Int. 41 (2015) 9863-9869
[9] N. Hazeri, S.S. Sajadikhah, M.T. Maghsoodlou, S. Mohamadian-Souri, M. Norozi, M. Moein, J. Chin. Chem. Soc. 61 (2014) 217-220.
[10] H. Zang, Y. Zhang, B. Cheng, W. Zhang, X. Xu, Y. Ren. Chin. J. Chem. 30 (2012) 362-366.
[11] P. Biginelli, Gazz. Chim. Ital. 23 (1893) 360-413.
[12] O. Prakash, R. Kumar, V. Parkash, Eur. J. Med. Chem. 43 (2008) 435-440.
[13] K.Sujatha, P. Shanmugam, P.T. Perumal, D. Muralidharan, M. Rajendran, Bioorg. Med. Chem. Lett. 16 (2006) 4893-4897.
[14] S. Wisen, J. Androsavich, C.G. Evans , L. Chang, J.E. Gestwicki , Bioorg. Med. Chem.  Lett. 18 (2008) 60-
65.
[15] L. Heys, C.G. Moore, P. Murphy, J. Chem. Soc. Rev. 29 (2000) 57-67.
[16] M. Ashok, B.S. Holla, N.S. Kumara, Eur. J. Med. Chem. 42 (2007) 380-385.
[17] E.W. Hurst, R. Hull, J. Med. Pharm. Chem. 3 (1961) 215-219.
[18] A.M. Magerramow, M.M. Kurbanova, R.T. Abdinbekova, I.A. Rzaeva, V.M. Farzaliev, M.A. Allokhverdiev, Russ. J. Appl. Chem. 79 (2006) 787-790.
[19] S.S. Bahekar, D.B. Shinde, Bioorg. Med. Chem. Lett. 14 (2004) 1733-1736.
[20] S. Chitra, K. Pandiarajan, Tetrahdron Lett. 50 (2009) 2222-2224.
[21] A. Rajack, K. Yuvaraju, C. Praveen, Y.L.N. Murthy, J. Mol. Catal. A: Chem. 370 (2013) 197-204.
[22] K. Konkala, N.M. Sabbavarapu, R. Katla, N.Y.V. Durga, T.V.K. Reddy, L.A.P.D. Bethala , R.B.N. Prasad, Tetrahedron Lett. 53 (2012) 1968-1973.
[23] D.L. Silva, S.A. Fernandes, A.A. Sabino, A. Fatima, Tetrahedron Lett. 52 (2011) 6328-6330.
[24] C.J. Liu, J.D. Wang, Molecules 14 (2009) 763-770.
[25] A. Debache, M. Amimour, A. Belfaitah, S. Rhouati, B. Carboni, Tetrahedron Lett. 49 (2008) 6119-6121.
[26] F. Shirini, M.A. Zolfigol, A. Albadi. Chin. Chem. Lett. 22 (2011) 318-321.
[27] A. Kumar, R.A. Maurya, Tetrahedron Lett. 48 (2007) 4569-4571.
[28] J. Lai, M. Sharma, S. Gupta, P. Parashar, P. Sahu, D.D. Agarwal, J. Mol. Catal. A: Chem. 352 (2012) 31-37.
[29] M. Litvic, I. Vecenaj, Z.M. Ladisic, M. Lovric, V. Vinkovic, M. Filipan-Litvic, Tetrahedron 66 (2010) 3463-3471.
[30] B. Ahmad, R.A. Khan, Habibullah, M. Keshai, Tetrahydron Lett. 50 (2009) 2889-2892.
[31] A. Kamal, T. Krishnaji, M.A. Azhar, Catal. Commun. 8 (2007) 1929-1933.
[32] Kappe, C.O.J. Org. Chem. 62 (1997) 7201-7204
[33] Y. Zhang, B. Wang, X. Zhang, J. Huang, C. Liu, Molecules 20 (2015) 3811-3820.
[34] P. Attri, R. Bhatia, J. Gaur, B. Arora, A. Gupta, N. Kumar, E.H. C hoi, Arab. J. Chem. (2014) doi: 10.1016/j.arabjc.2014.05.007.
[35] K. Aswin, S.S. Mansoor, K. Logaiya, P.N. Sudhan, R.N. Ahmed, J. Taibah University Sci. 8 (2014) 236-247.