Document Type: Original Article

Authors

Department of Chemistry, Payame Noor University, PO Box 19395-3697 Tehran, Iran

Abstract

In this research, the one-pot multi-component reaction of β-ketoesters with aryl aldehydes and urea/thiourea has been performed using a dual-functional ionic liquid-catalyst namely N1,N1,N2,N2-tetramethylethylenediaminium-N1,N2-disulfonic acid trifluoroacetate ([TMEDSA][TFA]2) in solvent-free conditions. By reason of dual-functionality of the catalyst (possessing acidic and basic sites), and also having two numbers of each site, it was highly effectual and general catalyst, and afforded the products {3,4-dihydropyrimidin-2-(1H)-ones and 3,4-dihydropyrimidin-2-(1H)-thiones} in short times with excellent yields. Moreover, a plausible mechanism based on dual-functionality of the catalyst has been proposed.

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Main Subjects

[1] Kappe C.O. Tetrahedron, 1993, 49:6937

[2] Kappe C.O., Fabian W.M.F., Semones M.A. Tetrahedron, 1997, 53:2803

[3] Kappe C.O. Acc. Chem. Res., 2000, 33:879

[4] Atwal K.S., Rovnyak G.C., Kimball S.D., Floyd D.M., Moreland S., Swanson B.N., Gougoutas D.Z., Schewartz J., Smillie K.M., Malley M.F. J. Med. Chem., 1990, 33:2629

[5] Nagarathnam D., Miao S.W., Lagu B., Chiu G., Fang J., Dhar T.G.M., Zhang J., Tyagarajan S., Marzabadi M. R., Zhang F., Wong W.C., Sun W., Tian D., Zhang J., Wetzel J.M., Forray C., Chang R.S.L., Broten T.P., Schorn T. W., Chen T.B., O'Malley S., Ransom R.W., Schneck K., Bendesky R., Harrell C.M., Gluchowski C. J. Med. Chem., 1999, 42:4764

[6] Patil A.D., Kumar N.V., Kokke W.C., Bean M.F., Freyer A.J., Brossi C.D., Mai S., Truneh A., Faulkner D.J., Carte B., Breen A.L., Hertzberg R.P., Johnson R.K., Westly J.W., Potts B.C.M. J. Org. Chem., 1995, 60:1182

[7] Snider B.B., Chen J., Patil A.D., Freyer A.J. Tetrahedron Lett., 1996, 37:6977

[8] Saher L., Makhloufi-Chebli M., Dermeche L., Boutemeur-Khedis B., Rabia C., Silva A.M.S., Hamdi M. Tetrahedron Lett., 2016, 57:1492

[9] Azuaje J., Tubío C.R., Escalante L., Gómez M., Guitián F., Coelho A., Caamaño O., Gil A., Sotelo E. Appl. Catal. A., 2017, 530:203

[10] Zare A., Nasouri Z. J.  Mol. Liq., 2016, 216:364

[11] Liu C.J., Wang J.D. Molecules, 2009, 14:763

[12] Hasaninejad A., Zare A., Jafari F., Moosavi-Zare A.R. E J. Chem., 2009, 6:459

[13] Dadhania A.N., Patel V.K., Raval D.K. J. Chem. Sci., 2012, 124:921

[14] Ramos L.M., Tobio A.Y.P.L., dos Santos M.R., de Oliveira H.C.B., Gomes A.F., Gozzo F.C., de Oliveira A.L., Neto B.A.D. J. Org. Chem., 2012, 77:10184

[15] Barbero M., Cadamuro S., Dughera S. Green Chem., 2017, 19:1529

[16] Prakash G.K.S., Lau H., Panja C., Bychinskaya I., Ganesh S.K., Zaro B., Mathew T., Olah G.A. Catal. Lett., 2014, 144:2012

[17] Mondal J., Sen T., Bhaumik A. Dalton Trans., 2012, 41:6173

[18] Chakraborty A., Majumdar S., Maiti D.K. Tetrahedron Lett., 2016, 57:3298

[19] Zolfigol M.A., Khazaei A., Moosavi-Zare A.R., Zare A., Kruger H.G., Asgari Z., Khakyzadeh V., Kazem-Rostami M. J. Org. Chem., 2012, 77:3640

[20] Ramli N.A.S., Amin N.A.S. Bioenergy Res., 2017, 10:50

[21] Moosavi-Zare A.R., Zolfigol M.A., Khaledian O., Khakyzadeh V., Darestani Farahani M.,  Beyzavi M.H., Kruger H.G. Chem. Eng. J., 2014, 248:122

[22] Zare A., Yousofi T., Moosavi-Zare A.R. RSC Adv., 2012, 2:7988

[23] Zare A., Sharif E., Arghoon A., Ghasemi M., Dehghani B., Ahmad-Zadeh S., Zarei F. Iran. J. Catal., 2017, 7:233

[24] Z. Kordrostami, Zare A. J. Appl. Chem. Res., 2018, 12:42

[25] Moosavi-Zare A.R., Zolfigol M.A., Zarei M., Zare A., Afsar J. Appl. Catal. A., 2015, 505:224

[26] Shahbazi R., F.K. Behbahani F.K. Chem. Method., 2018, 2:270

[27] Javahershenas R., Khalafy J. Asian J. Green Chem., 2018, 2:318

[28] Mohammadi B., Salmani L. Asian J. Green Chem., 2018, 2:51

[29] Hassani H., Zakerinasab B., Nozarie A. Asian J. Green Chem., 2018, 2:59

[30] Singh K.,  Sharma S. Tetrahedron Lett., 2017, 58:197

[31] Zare A., Merajoddin M., Moosavi‐Zare A.R., Zarei M. Chin. J. Catal., 2014, 35:85

[32] Arzehgar Z., Aydi A., Mirzaei Heydari M. Asian J. Green Chem., 2018, 2:281

[33] Sajjadifar S., Mansouri G., Miraninezhad S. Asian J. Nanosci. Mater., 2018, 1:11

[34] Rezayati S., Hajinasiri R., Hossaini Z., Abbaspour S. Asian J. Green Chem., 2018, 2:268