Document Type: Original Research Article

Authors

1 Department of Organic Chemistry, University of Guilan, Rasht, Iran

2 Department of Chemistry, Tonekabon Branch, Islamic Azad University, Tonekabon, Iran

3 aDepartment of Organic Chemistry, Faculty of Sciences, University of Guilan, Rasht, Iran

4 University of Guilan

Abstract

In this work, Nano TiO2@KSF used as an efficient, homogeneous and reusable catalyst for the synthesis of pyrano[2,3-d]-pyrimidinone derivatives via three-component reactions between malononitrile, barbituric acid and various aldehydes in water. The products were formed in high yields within short reaction times. Also, this catalyst can be reused several times without loss of its catalytic activity. All the products were characterized using melting point and a variety of techniques, including infrared spectra (FT-IR) and were compared with trusty references. This method a simple, efficient and green for the preparation of pyrano[2,3-d]pyrimidinone (4a-4l) derivatives using TiO2@KSF under mild conditions. The promising reasons for the presented method is efficiency, generality reaction profile, mild and green reaction conditions, easy work-up procedure, short reaction times and high yields of the products, ease of preparation.

Graphical Abstract

Keywords

Main Subjects

[1] R.W. Armstrong, A.P. Combs, P.A. Tempest, S.D. Brown, T.A. Keating, Acc. Chem. Res., 1996, 29, 123-131.

[2] Y.A. Ibrahim, H. Behbehani, M.R. Ibrahim, Tetrahedron Lett., 2002, 43, 4207-4210.

[3] E. Tabrizian, A. Amoozadeh, S. Rahmani, E. Imanifar, S. Azhari, M. Malmir, Chin. Chem. Lett., 2015, 26, 1278-1282.

[4] M. Mohammadi Zeydi, N.O. Mahmoodi, Int. J. Nano. Dimens., 2016, 7, 174-180.

[5] A.D. Broom, J.L. Shim, G.L. Anderson, J. Org. Chem., 1976, 41, 3027–3030.

[6] E.M. Griva, S. Lee, C.W. Siyal, D.S. Duch, C.A. Nichol, J. Med. Chem., 1980, 23, 327-329.

[7] D. Heber, C. Heers, U. Ravens, Pharmazie., 1993, 48, 537-541.

[8] M.M. Ghorab, A.Y. Hassan, Phosphorus Sulfur Silicon., 1998, 141, 251-261.

[9] V. K. Ahluwalia, R. Kumar, K. Khurana, R. Batla. Tetrahedron., 1990, 46, 3953-3962.

[10] N. Sheikhan-Shamsabadi, M. Ghashang, Main. Group. Metal. Chemistry., 2017, 40, 19-25.

[11] M.M. Heravi, A. Ghods, K. Bakhtiari, F. Derikvand, Synth. Commun., 2010, 40, 1927-1931.

[12] A. Mobinikhaledi, N. Foroughifar, M.A. Bodaghi Fard, Synth. React. Inorg. Metal Org. Nano Metal Chem,. 2010, 40, 179-185.

[13] J. Azizian, A. Shameli, S. Balalaie, M.M. Ghanbari, S. Zomorodbakhsh, M. Entezari, S. Bagheri, G. Fakhrpour, Orient. J. Chem., 2012, 28, 327-332.

[14] A.R. Bhat, A.H. Shalla, R.S. Dongre, J. J. Taibah. Univ. Sci., 2016, 10, 9-18.

[15] A. Mobinikhaledi, M.A. Bodaghi Fard, Acta Chim. Slov. 2010, 57, 931-935.

[16] N. Seyyedi, F. Shirini, M.S.N. Langarudi,. RSC. Advances., 2016, 6, 44630-44640.

[17] H. Kefayati, M. Valizadeh, A. Islamnezhad, Anal. Bioanal. Electrochem., 2014, 6, 80-90.

[18] G. Mohammadi Ziarani, S. Faramarzi, S. Asadi, A. Badiei, R. Bazl, M. Amanlou, DARU J. Pharm. Sci., 2013, 21, 1-13.

[19] O. Goli-Jolodar, F. Shirini, M. Seddighi, J. I. C. S. 2016, 13, 457-463.

[20] N.O. Mahmoodi, M. Mohammadi Zeydi, E. Biazar, J. Sulfur. Chem., 2016, 37, 613-621.

[21] M. Mohammadi Zeydi, S. Ahmadi, Orient. J. Chem., 2016, 32, 2215-2220.

[22] N.O. Mahmoodi, M. Mohammadi Zeydi, E. Biazar, Z. Kazeminejad, Phosphorus Sulfur Silicon Relat. Elem., 2017, 192, 344-350.

[23] N.O. Mahmoodi, M. Mohammadi Zeydi, M. Mamaghani, N. Montazeri, Res. Chem. Intermed., 2017, 43, 2641-2651.

[24] N.O. Mahmoodi, Z. Khazaei, M. Mohammadi Zeydi. J. Iran. Chem. Soc., 2017. 1-10

[25] B. Sabour, M. H. Peyrovi, M. Hajimohammadi. Res. Chem. Intermed., 2015, 41, 1343-1350.

[26] B. Sadeghi, M. Bouslik, M. R. Shishehbore. J. Iran. Chem. Soc., 2015, 12, 1801-1808.

[27] J. Albadi, A. Mansournezhad, T. Sadeghi. Res. Chem. Intermed., 2015, 41, 8317-8326.