Document Type: Original Research Article

Authors

1 Department of Chemistry, Payame Noor University, PO Box 19395-4697, Tehran, Iran

2 Laboratory of Advanced Catalysis for Sustainability, School of Chemistry, The University of Sydney, Sydney 2006, Australia

Abstract

One-pot synthesis of Hantzsch 1,4-dihydropyridines (1,4-DHP) under solvent-free conditions catalyzed by HKUST-1 metal-organic frameworks are reported here. This method provides 1,4-dihydropyridines in good to excellent yields with little catalyst loading. The present methodology offers several advantages, including ease of the preparation and handling of the catalyst, simple and easy work-up, short reaction times, high yields of the products and recyclability of the catalyst.
One-pot synthesis of Hantzsch 1,4-dihydropyridines (1,4-DHP) under solvent-free conditions catalyzed by HKUST-1 metal-organic frameworks are reported here. This method provides 1,4-dihydropyridines in good to excellent yields with little catalyst loading. The present methodology offers several advantages, including ease of the preparation and handling of the catalyst, simple and easy work-up, short reaction times, high yields of the products and recyclability of the catalyst.

Graphical Abstract

Keywords

Main Subjects

[1]. Chughtai A.H., Ahmad N., Younus H.A., Laypkov A., Verpoort F. Chem. Soc. Rev., 2015, 44:6804

[2]. Deria P., Mondloch J.E., Karagiaridi O., Bury W., Hupp J.T., Farha O.K. Chem. Soc. Rev., 2014, 43:5896

[3]. Dhakshinamoorthy A., Asiri A.M., Garcia H. Chem. Soc. Rev., 2015, 44:1922

[4]. Xamena F.X.L.I., Abad A., Corma A., Garcia H. J. Catal., 2007, 250:294

[5]. Gao S., Zhao N., Shu M., Che S. Appl. Catal. A: Gen., 2010, 388:196

[6]. Nguyen L.T.L., Nguyen C.V., Dang G.H., Le K.K.A., Phan N.T.S. J. Mol. Catal. A. Chem., 2011, 349:28

[7]. Yang J., Li P., Wang L. Catal. Commun., 2012, 27:58

[8]. Li P., Regati S., Butcher R.J., Arman H.D., Chen Z., Xiang S., Chen B., Zhao C.G. Tetrahedron Lett., 2011, 52:6220

[9]. Oxford G.A.E., Dubbeldam D., Broadbelt L.J., Snurr R.Q. J. Mol. Catal. A. Chem., 2011, 334:89

[10]. Song J., Zhang Z., Hu S., Wu T., Jiang T., Han B. Green Chem., 2009, 11:1031

[11]. Song F., Wang C., Falkowski J.M., Ma L., Lin W. J. Am. Chem. Soc., 2010, 132:15390

[12]. Dhakshinamoorthy A., Alvaro M., Garcia H. ACS Catal., 2011, 1:48

[13]. Nguyen H.G.T., Weston M.H., Farha O.K., Hupp J.T., Nguyen S.T. Cryst. Eng. Commun. A., 2012, 4:4115

[14]. Puthiaraj P., Suresh P., Pitchumani K. Green Chem., 2014, 16:2865

[15]. Zhou Y., Song J., Liang S., Hu S., Liu H., Jiang T., Han B. J. Mol. Catal. A., 2009, 308:68

[16]. Song P., Li Y., Li W., He B., Yang J., Li X. Int. J. Hydrogen Energy., 2011, 36:10468

[17]. Savonnet M., Aguado S., Ravon U., Bazer-Bachi D., Lecocq V., Bats N., Pinel C., Farrus-seng D. Green Chem., 2009, 11:1729

[18]. Luz I., Xamena F.X.L.I.A. Corma J. J. Catal., 2010, 276:134

[19]. Sajjadifar S., Arzehgar Z., Ghayuri A. J. Chin. Chem. Soc., 2017, 65:205

[20]. Sajjadifar S., Arzehgar Z., Khoshpoori S. J. Inorg. Organomet. Polym. Mate., 2017, 1:10

[21]. Sausins A., Duburs G. Heterocycles, 1988, 27:269

[22]. Lavilla R. J. Chem. Soc. Perkin Trans., 2002, 1:1141

[23]. Edraki N., Mehdipour A.R., Khoshneviszadeh M., Miri R. Drug Discov. Today, 2009, 14:1058

[24]. Herrera R.P. Top. Curr. Chem., 2016, 374:29

[25]. Hantzsch A. Ber. Dtsch. Chem. Ges., 1881, 14:1637

[26]. Fowler F.W. J. Org. Chem., 1972, 37:1321

[27]. Sharma M., Aggarwal N., Rawat D.S. J. Heterocycl. Chem., 2008, 45:737

[28]. Zonouz A.M., Hosseini S.B. Synth. Commun., 2008, 38:290

[29]. Rafiee E., Eavani S., Rashidzadeh S., Joshaghani M. Inorg. Chim. Acta, 2009, 362:3555

[30]. Debache A., Ghalem W., Boulcina R., Belfaitah A., Rhouati S., Carboni B. Tetrahedron Lett., 2009, 50:5248

[31]. Sabitha G., Arundhathi K., Sudhakar K., Sastry B.S., Yadav J.S. Synth. Commun., 2009, 39:2843

[32]. Debache A., Boulcina R., Belfaitah A., Rhouati S., Carbonib B. Synlett, 2008, 2008:509

[33]. Ko S., Sastry M.N.V. Lin C., Yao C.F. Tetrahedron Lett., 2005, 46:5771

[34]. Chari M.A., Syamasundar K. Catal. Commun., 2005, 6:624

[35]. Rouhani F., Morsali A. New J. Chem., 2017, 41:15475

[36]. Cepanec I., Litvić M., Bartolinčić A., Lovrić M. Tetrahedron, 2005, 61:4275

[37]. Yadav J., Reddy B.S., Premalatha K., Shankar K.S. Can. J. Chem., 2008, 86:124

[38]. Paraskar A.S., Dewkar G.K., Sudalai A. Tetrahedron Lett., 2003, 44:3305

[39]. Chui S.S.Y., Lo S.M.F., Charmant J.P.H., Orpen A.G. Williams ID. Science 1999, 283:1148

[40]. Soleiman-Beigi M., Arzehgar Z. Synlett, 2018, 29: 986

[41]. Nguyen L.T.L., Nguyen T.T., Nguyen K.D., Phan N.T.S. Appl. Catal. A., 2012, 425:44

[42]. Ho S.L., Yoon I.C., Cho C.S., Choi H.J. J. Organometal. Chem., 2015, 791:13

[43]. Soleiman-Beigi M., Yavari I., Sadeghizadeh F. RSC Adv., 2015, 5:87564

[44]. Lenardo E.J., Lara R.G., Silva M.S., Jacob R.G., Perin G. Tetrahedron Lett., 2007, 48:7668

[45]. Soleiman-Beigi M., Arzehgar Z. Monatsh Chem., 2016, 147:1759

[46]. S. Rezayati, Sajjadifar S. J. Sci. I. R. Iran., 2014, 25:329

[47]. Sajjadifar S. Chem. Method., 2017, 1:1

[48]. Sajjadifar S., Rezayati S. Chem. Pape., 2014, 68:531

[49]. Kumar P., Hussain K., Kumar A. Curr. Chem. Lett., 2014, 3:75