Methyl-1-sulfonic acid imidazolium chloride as a highly efficient catalyst for the solvent-free synthesis of 3,4-dihydropyrimidin-2(1H)-ones

Document Type : Research Paper

Authors

Department of Chemistry, Payame Noor University (PNU), P.O. Box 19395-4697, Tehran, Iran

Abstract

3,4--Dihydropyrimidin-2(1H)-ones are an important class of heterocyclic compounds, and possess many pharmaceutical and biological activity, such as antitumor, antibacterial, antiviral properties. These heterocycles are essential moiety of SWO2 and SQ32547 structures which possess antihypertensive property. In addition, dihydropyrimidines are essential backbones of calcium channel blockers. In this research, a new and highly efficient method for the synthesis of 3,4-dihydropyrimidin-2(1H)-ones via one-pot-multi-component reaction between β-ketoesters, aromatic aldehydes and urea in the presence of acidic ionic liquid 3-methyl-1-sulfonic acid imidazolium chloride ([Msim]Cl)under solvent-free conditions have been introduced. These reactions has completed in 20 min. In this method, these compounds have been prepared in excellent yields. The advantages of this protocol are efficiency, generality, high yields of the products, short reaction times, simplicity, low cost, easy preparation of the catalyst, and performing the reactions in solvent-free conditions.
The advantages of this protocol are efficiency, generality, high yields of the products, short reaction times, simplicity, low cost, easy preparation of the catalyst, and performing the reactions in solvent-free conditions.  

Keywords


[1] Haggarty S. J., Mayer T. U., Miyamoto D. T., Fathi R., King R. W., Mitchison T. J., Schreiber S. L., Dissecting cellular processes using small molecules: identification of colchicine-like, taxol-like and other small molecules that perturb mitosis, Chem. Biol., 2000, 7, 275-286.
 
[2] Aron Z. D., Overman L. E., The tethered Biginelli condensation in natural product synthesis, Chem. Commun., 2004, 253-265.
 
[3] Yarim M., Sarac S., Kilic F. S., Erol K., Synthesis and in vitro calciumantagonist activity of 4-aryl-7,7-dimethyl/1,7,7-trimethyl-1.2,3,4,5,6,7,8-octahydroquinazoline-2,5-dione derivatives, Il Farmaco, 2003, 58, 17-24.
 
[4] Kappe C. O., Biologically active dihydropyrimidones of the Biginelli-type- a literature survey, Eur. J. Med. Chem., 2000, 35, 1043-1052.
[5] Byk G., Gettlieb H. E., Herscovici J., Mirkin F., New regioselective multicomponent reaction: one pot synthesis of Spiro hetero-bicyclic aliphatic rings, J. Comb. Chem., 2000, 2, 732-735.
 
[6] Jetti S. R., Bhatewara A., Kadre T., Jai S., Silica-bonded N-propyl sulfamic acid as an efficient recyclable catalyst for the synthesis of 3,4-dihydropyrimidin-2-(1H)-ones/thiones under heterogeneous conditions, Chin. Chem. Lett., 2014, 25, 469-473.
 
[7] Zhang Y., Wang B., Zhang X., Huang J., Liu, C., An efficient synthesis of 3,4-dihydropyrimidin-2(1H)-ones and thiones catalyzed by a novel Brønsted acidic ionic liquid under solvent-free conditions, Molecules, 2015, 20, 3811-3820.
 
[8] Saher L., Makhloufi-Chebli M., Dermeche L., Boutemeur-Khedis B., Rabia C., Silva A. M. S., Hamdi M., Keggin and Dawson-type polyoxometalates as efficient catalysts for the synthesis of 3,4-dihydropyrimidinones: experimental and theoretical studies, Tetrahedron Lett., 2016, 57, 1492-1496.
 
[9] Kolvari E., Koukabi N., Armandpour O., A simple and efficient synthesis of 3,4-dihydropyrimidin-2-(1H)-ones via Biginelli reaction catalyzed by nanomagnetic-supported sulfonic acid, Tetrahedron, 2014, 70, 1383-1386.
 
[10] Hasaninejad A., Zare A., Jafari F., Moosavi-Zare A. R., P2O5/SiO2 as an efficient, green and heterogeneous catalytic system for the solvent-free synthesis of 3,4-dihydropyrimidin-2-(1H)-ones (and -thiones), E-J. Chem., 2009, 6, 459-465
 
[11] Fu N. Y., Yuan Y. F., Cao Z., Wang S. W., Wang J. T., Peppe C., Indium (III) bromide-catalyzed preparation of dihydropyrimidinones: improved protocol conditions for the Biginelli reaction, Tetrahedron, 2002, 58, 4801-4808.
[12] Mohammadpour Amini M., Shaabani A., Bazgir A., Tangstophosphoric acid (H3PW12O40): An efficient and eco-friendly catalyst for the one-pot synthesis of dihydropyrimidin-2(1H)-ones, Catal. Commun., 2006, 7, 843-847.
 
[13] Farhadi A., Noei J., Aliyari R. H., Albakhtiyari M., Takassi M. A., Experimental and theoretical study on a one-pot, three-component route to 3,4-dihydropyrimidin-2(1H)-ones/thiones TiCl3OTf-[bmim]Cl, Res. Chem. Intermed., 2016, 42, 1401-1409.
 
[14] Moghaddasi M., Davoodnia A., Heravi M. M., Tavakili-Hoseini N., Sulfonated carbon catalyzed Biginelli reaction for one-pot synthesis of 3,4-dihydropyrimidin-2(1H)-ones and -thiones, Chin. J. Catal., 2012, 33, 706-710.
 
[15] Ahmadi T., Mohammadi Ziarani G., Gholamzadeh P., Mollabagher H., Recent advances in asymmetric multicomponent reactions (AMCRs), Tetrahedron: Asym., 2017, 28, 708-724.
 
[16] Zare A., Abi F., Moosavi-Zare A. R., Beyzavi M. H., Zolfigol M. A., Synthesis, characterization and application of ionic liquid 1,3-disulfonic acid imidazolium hydrogen sulfate as an efficient catalyst for the preparation of hexahydroquinolines, J. Mol. Liq., 2013, 178, 113-121.
 
[17] Kalita S. J., Bayan R., Devi J., Brahma S., Mecadon H., Deka D. C., A new, convenient and expeditious synthesis of 4-alkyl-5-methyl-1H-pyrazol-3-ols in water through a multicomponent reaction, Tetrahedron Lett., 2017, 58, 566-569.
 
[18] BronycaClare A. S., MacFarlane D. R., Ionic Liquids (Topics in Current Chemistry), Kirchner B. (Ed.), Springer, 2010.
 
[19] Wasserscheid P., Welton T., Ionic Liquids in Synthesis, Wiley-VCH, Weinheim, 2008.
 
[20] Zolfigol M. A., Khazaei A., Moosavi-Zare A. R., Zare A., Khakyzadeh V., Rapid synthesis of 1-amidoalkyl-2-naphthols over sulfonic acid functionalized imidazolium salts, Appl. Catal. A: Gen., 2011, 400, 70-81.
 
[21] Ahmadi S., Zare A., Aali-Hosaini M., Maghsoudi M., Izadpanah S., Parhami A., Merajoddin M., Design, characterization, and use of N,N-diethyl-N-sulfoethanaminium hydrogen sulfate {[Et3N-SO3H]HSO4} as a novel and highly efficient catalyst for preparation of α,α´-bis(arylidene)cycloalkanones, Res. Chem. Intermed., 2016 42, 6245-6253
 
[22] Zare A., Ahmadi S., Abi F., Hekmat-Zadeh T., Merajoddin M., Hatami M., Keshtkar M. and Khazaei A., Characterization and application of pyrazinium di(hydrogen sulfate) as a highly efficient catalyst for synthesis of 14-aryl-14H-dibenzo[a,j]xanthenes, 9-aryl-1,8-dioxo-octahydroxanthenes and 1-amidoalkyl/carbamatoalkyl-2-naphthols, Sci. Iran. C, 2015, 22, 2271-2281.
 
[23] Peng Q., Mahmood K., Wu Y., Liu Z., Wei L., Yuan H., Yang R., Effective binary catalysts of Brønsted acidic ionic liquids and stannous chloride dihydrate for melt polycondensation of L-lactic acid, Mol. Catal., 2017, 434, 140-145.
 
[24] Tao D.-J., Dong Y., Cao Z.-J., Chen F.-F., Chen X.-S., Huang K., Tuning the acidity of sulfonic functionalized ionic liquids for highly efficient and selective synthesis of terpene esters, J. Indust. Engin. Chem., 2016, 41, 122-129.