Multi-component preparation of diethyl/methyl 1,3-diaryl-1,2,3,6-tetrahydro-pyrimidine-4,5-dicarboxylates using hydrated phosphomolybdic acid as an efficient catalyst
الموضوعات : Iranian Journal of CatalysisMehdi Abaszadeh 1 , Mohammad Seifi 2 , Majid Ghashang 3
1 - Pharmaceutics Research Center, Kerman University of Medical Sciences, Kerman 76175-493, Iran.
2 - Department of Chemistry, Faculty of Sciences, Najafabad Branch, Islamic Azad University, Najafabad, Esfahan, Iran; P.O. Box: 517
3 - Department of Chemistry, Faculty of Sciences, Najafabad Branch, Islamic Azad University, Najafabad, Esfahan, Iran; P.O. Box: 517
الکلمات المفتاحية: Tetrahydropyrimidine, Dialkylacetylene dicarboxylate, H3[P(Mo3O10)4].xH2O,
ملخص المقالة :
The synthesis of diethyl/methyl 1,3-diaryl-1,2,3,6-tetrahydro-pyrimidine-4,5-dicarboxylates can be achieved using one-pot reaction from dialkylacetylene dicarboxylate, amines, and formaldehyde by employing hydrated phosphomolybdic acid (H3[P(Mo3O10)4].xH2O) as catalyst at room temperature. The effect of various solvent and catalyst amount was investigated. The salient features of the present method are: simple and straightforward work-up, cost-effective and environmentally benign procedure. The obtained yield of products was in the range of 75-92%. Based on the obtained results, the steric effects of the substituents in dialkylacetylene dicarboxylates played significant role in the rate of the reaction. When diethylacetylene dicarboxylate were used in this process, the corresponding product was obtained in good yields but in longer reaction time. Electron donating group on the amine was able to facilitate the transformation by giving evidently shorter reaction times.
[1] P.G. Baraldi, M.A. Tabrizi, S. Gessi, P.A. Borea, Chem. Rev. 108 (2008) 238-263.
[2] C.O. Kappe, A. Stadler, Org. React. 63 (2004) 1-116.
[3] C.O. Kappe, Acc. Chem. Res. 33 (2000) 879-888.
[4] (a) I.M. Lagoja, Chem. Biodivers. 2 (2005) 1-50; (b) C.O. Kappe, Eur. J. Med. Chem. 35 (2000) 1043-1052.
[5] S.N. Darandale, D.N. Pansare, N.A. Mulla, D.B. Shinde, Bioorg. Med. Chem. Lett. 23 (2013) 2632-2635.
[6] S. Wisen, J. Androsavich, C.G. Evans, L. Chang, J.E. Gestwicki, Bioorg. Med. Chem. Lett. 18 (2008) 60-65.
[7] B.C. Raju, R. Nageswara Rao, P. Suman, P. Yogeeswari, D. Sriram, T. Basha Shaik, S.V. Kalivendi, Bioorg. Med. Chem. Lett. 21 (2011) 2855-2859.
[8] C.G. Evans, S. Wisen, J.E. Gestwicki, J. Biol. Chem. 281 (2006) 33182-33191.
[9] Q. Zhu, H. Jiang, J. Li, M. Zhang, X. Wang, C. Qi, Tetrahedron 65 (2009) 4604-4613.
[10] H. Cao, X. Wang, H. Jiang, Q. Zhu, M. Zhang, H. Liu, Chem. Eur. J. 14 (2008) 11623-11633.
[11] B. Das, B. Shashi Kanth, D. Balaji Shinde, V.T. Kamble, Helv. Chim. Acta 94 (2011) 2087-2091.
[12] M. Ghashang, Curr. Org. Synth. 9 (2012) 727-732.
[13] M. Ghashang, Lett. Org. Chem. 9 (2012) 497-502.
[14] M.R. Mohammad Shafiee, M. Ghashang, A. Fazlinia, Curr. Nanosci. 9 (2013) 197-201.
[15] M. Ghashang, Res. Chem. Intermed. 39 (2013) 2187-2195.
[16] M. Ghashang, Res. Chem. Intermed. 39 (2013) 2837-2842.
[17] M. Dehbashi, M. Aliahmad, M.R. Mohammad Shafiee, M. Ghashang, Synth. React. Inorg. Met. Org. Chem. 43 (2013) 1301-1306.
