Document Type : Original Research Article
Authors
- Govardhan Duguta 1
- Satish Kumar Mukka 1
- Hemanth Sriram Yelike 1
- Chinna Rajanna Kamatala 1
- Sai Sudhakar Mukka 2
1 Department of Chemistry, Osmania University, Hyderabad-500 007, Telangana, India
2 Department of Chemistry, BITS Pilani, Hyderabad Campus, Hyderabad-500078, T.S. India
Abstract
In the present study, we have accomplished N,N’-dimethyl formamide (DMF)/trichloroisocyanuric acid and DMF/trichlorotriazine as efficient catalysts for the synthesis of 3,4-dihydropyrimidinones/thiones from one-pot multi-component reaction of β-ketoester, aromatic aldehydes, and urea under reflux condition. The reaction operates also under solvent free microwave condition. The results obtained from this study were compared with those obtained from classical Vilsmeier-Haack adducts (DMF/POCl3 and DMF/SOCl2) as catalysts. Reaction times and product yields observed in this study indicated shorter reaction times and better product yields with modified VH reagents (TCCA/DMF and TCTA/DMF) over classical VH reagents (POCl3/DMF and SOCl2/DMF). The catalytic activity of (TCTA/DMF)>(TCCA/DMF)>(POCl3/DMF>SOCl2/DMF).
Graphical Abstract
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Keywords
- DMF/trichloroisocyanuric acid DMF/trichlorotriazine Green Vilsmeier
- Haack reagents Rate enhancements Microwave assisted reactions
Main Subjects
[1]. Biginelli P. Ber. Dtsch. Chem. Ges, 1891, 24:1317
[2]. Morita H., Sato Y., Chan K.L., Choo C.Y., Itokawa H., Takeya K., Kobayashi J. J. Nat. Prod., 2000, 63:1707
[3]. Rosowsky A., Huang P.C., Papathanasopoulos N., Modest E., Quinazolines J. J. Med. Chem., 1974, 17:1217
[4]. Godde F., Toulme J.J., Moreau S. Biochemistry, 1998, 37:13765
[5]. Dai Y., Cao M., Zhuang M., Xia S., Tu S., Rong L. Synthet. Commun., 2011, 41:3039
[6]. Wang X., Quan Z., Wang F., Wang M., Zhang Z., Li Z. Synthet. Commun., 2006, 36:451
[7]. Lei M., Wu D.D., Wei H.G., Wang Y.G. Synthet. Commun., 2009, 3:475
[8]. Xu F., Wang J.J., Tian Y.P. Synthet. Commun., 2008, 38:1299
[9]. Lin H.X., Zhao Q.J., Xu B., Wang X.H. Chinese Chem. Lett., 2007, 18:502
[10]. Konkala K., Sabbavarapu N.M., Katla R., Durga N.Y.V., Kumar Reddy V., Bethala L.A., Devi P., Prasad R.B.N. Tetrahedron Lett., 2012, 53:1968
[11]. Garima, Srivastava P.V., Yadav L.D.S. Tetrahedron Lett., 2010, 51:6436
[12]. Li M., Guo W.S., Wen L.R., Li Y.F. J. Mol. Catal. A Chem., 2006, 258:133
[13]. Peng J., Deng Y. Tetrahedron Lett., 2001, 42:5917
[14]. Dong F., Jun L., Xinli Z., Zhiwen Y., Zuliang L. J. Mol. Catal. A Chem., 2007, 274:208
[15]. Yadav L.D.S., Rai A., Rai V.K., Awasthi C. Tetrahedron, 2008, 64:1420
[16]. Alvim H.G.O., Lima T.B., Oliveira H.C.B., Gozzo F.C., Macedo J.L., Abdelnur P.V., Silva W.A., Neto B.A.D. ACS Catal., 2013, 3:1420
[17]. Elhamifar D., Nasr Esfahani M., Karimi B., Moshkelgosha R., Shabani A. Chem. Cat, 2014, 6:2593
[18]. Elhamifar D., Shabani A. Chem. A Eur. J., 2014, 20:3212
[19]. Shirini F., Abedini M., Pourhasan-Kisomi R. Chinese Chem. Lett., 2014, 25:111
[20]. Gong K., Wang H., Wang S., Ren X. Tetrahedron, 2015, 71:4830
[21]. Kouachi K., Lafaye G., Pronier S., Bennini L., Menad S. J. Mol. Catal. A Chem., 2014, 395:210
[22]. Rupali L.M., Prashant B.T., Pratima B.T., Vinod V.T., Bhagawan R.P., Rajendra P.P. Chinese Chem. Lett., 2013, 24:1070
[23]. Girija D., Bhojya Naik H.S., Vinay Kumar B., Sudhamani C.N., Harish K.N. Arabian J. Chem., 2019, 12:420
[24]. Zeba N.S. C. R. Chim., 2013, 16:183
[25]. Li P., Regati S., Butcher R.J., Arman H.D., Chen Z., Xiang S., Chen B. Zhao C.G. Tetrahedron Lett., 2011, 52:6220
[26]. Maryam M. C. R. Chim., 2012, 15:444
[27]. Jacob T.S., Thomas J.L., Ram Mohan S. Tetrahedron Lett., 2013, 54:983
[28]. Liu Q., Pan N., Xu J., Zhang W.W., Kong F. Synthet. Commun., 2013, 43:139
[29]. Slimi H., Moussaoui Y., Salem R. Arabian J. Chem., 2016, 9:S510
[30]. Yuan H., Zhang K., Xia J., Hu X., Yuan S. Cogent Chem., 2017, 3:1318692
[31]. Fu R., Yang Y., Lai W., Yongfeng M., Chen Z., Zhou J., Chai W., Wang Q., Yuan R. Synthet. Commun., 2015, 45:467
[32]. Bigdeli M.A., Gholami G., Sheikhhosseini E. Chinese Chem. Lett., 2011, 22:903
[33]. Wang D.C., Guo H.M., Qu G.R. Synthet. Commun., 2010, 40:1115
[34]. Harikrishnan P.S., Rajesh S.M., Perumal S., Almansour A.I. Tetrahedron Lett., 2013, 54:1076
[35]. Chen W.Y., Qin S.D., Jin J.R. Synthet. Commun., 2007, 37:47
[36]. Vilsmeier A., Haack A. Berich. Deutsch. Chem. Gesellsch, 1927, 60:119
[37]. Awad I.M.A. Monatsh. Chemie., 1990, 121:1023
[38]. Awad I.M.A. J. Chem. Tech. Biotechnol., 1993, 56:339
[39]. Su W., Weng Y., Li J., Yang Y., Zhao L., Chen Z., Li Z. Org. Preparat. Proced. Int., 2010, 42:503
[40]. Rajanna K.C., Satish Kumar M., Venkanna P., Ramgopal S., Venkateswarlu M. Int. J. Org. Chem., 2011, 1:250
[41]. Satish Kumar M., Rajendar Reddy K., Rajanna K.C., Venkanna P., Krishnaiah G. Synthes. React. Inorg. Met. Org. Nano Met. Chem., 2013, 43:977
[42]. Chakradhar A., Roopa R., Rajanna K.C., Saiprakash P.K. Synthet. Commun., 2009, 39:1817
[43]. Satish Kumar M., Rajanna K.C., Venkanna P., Venkateswarlu M. Tetrahedron Lett., 2014, 55:1756
[44]. (a) Venkateswarlu M., Satish Kumar M., Ramgopal S., Rajanna K.C., Umesh Kumar U., Uppalaiah K., Saiprakash P.K. Helv. Chim. Acta., 2011, 94:2168 (b) Rajanna K.C., Venkateswarlu M., Satish Kumar M., Umesh Kumar U., Venkateswarlu G., Saiprakash P.K. Int. J. Chem. Kinet., 2013, 45:69
[45]. Venkateswarlu M., Rajanna K.C., Satish Kumar M., Umesh Kumar U., Ramgopal S., Saiprakash P.K. Int. J. Org. Chem., 2011, 1:233
[46]. Rajanna K.C., Venkanna P., Satish Kumar M., Ramgopal S. Int. J. Org. Chem., 2012, 2:336
[47]. Satish Kumar M., Venkanna P., Ramgopal S., Ramesh K., Venkateswarlu M., Rajanna K.C. Org. Commun., 2012, 5:42
[48]. Satish Kumar M., Rajanna K.C., Venkanna P., Venkateswarlu M., Sudhakar chary V. Synthes. React. Inorg. Met. Org. Nano Met. Chem., 2016, 46:642
[49]. Venkanna P., Satish Kumar M., Rajanna K.C., Moazzam A.M. Synthes. React. Inorg. Met. Org. Nano Met. Chem., 2015, 45:97
[50]. Satish Kumar M., Rajanna K.C., Venkateswarlu M., Venkanna P., Saiprakash P.K. Synthet. Commun., 2015, 45:2251
[51]. Muddam B., Venkanna P., Venkateswarlu M., Satish Kumar M., Rajanna K.C. Synlett, 2018, 29:85
[52]. Rajack A., Yuvaraju K., Praveen C., Murthy Y.L.N. J. Mol. Catal. A Chem., 2013, 370:197
[53]. Debache A., Amimour M., Belfaitah A., Rhouati S., Carboni B. Tetrahedron Lett., 2008, 49:6119
[54]. Slimi H., Moussaoui Y., Salem R. Arabian J. Chem., 2016, 9:S510
[55]. Srinivasa Rao J., Verma D., Jain S. Arabian J. Chem., 2017, 10:S3184
[56]. Tayebee R., Ghadamgahi M. Arabian J. Chem., 2017, 10:S757
[57]. Gupta R., Paul S., Gupta R. J. Mol. Catal. A Chem., 2007, 266:50
[58]. Dhumaskar K.L., Meena S.N., Ghadi S.C., Tilve S.G. Bioorg. Med. Chem. Lett., 2014, 24:2897
[59]. Vasconcelos A., Oliveira P.S., Ritter M., Freitag R.A., Romano R., Quina F.H., Pizzuti L., Pereira C.M.P., Stefanello F.M., Barschak A.G. J. Biochem. Mol. Toxic., 2012, 26:155
[60]. Liberto N.A., Silva S.P., Fatima A., Fernandes S.A. Tetrahedron, 2013, 69:8245
[61]. Luo G., Liu C., Zhou H., He M. Lett. Org. Chem., 2006, 3:225
[62]. Patil S., Jadhav S.D., Mane S.Y. Int. J. Org. Chem., 2011, 1:125
[63]. Verma S., Jain S.L., Sain B. Tetrahedron Lett., 2010, 51:6897
[64]. Yu Y., Liu D., Liu C., Luo G. Bioorg. Med. Chem. Lett., 2007, 17:3508
[65]. Murthy Y.L.N., Rajack A., Yuvaraj K. Arabian J. Chem., 2016, 9:S1740
[66]. Slimi H., Moussaoui Y., Salem R. Arabian J. Chem., 2016, 9:S510
[67]. Attri P., Bhatia R., Gaurb J., Arora B., Gupta A., Kumar N., Choi E.H. Arabian J. Chem., 2017, 10:206
[68]. Varma R.S., Clark D.E., Sutton W.H., Lewis D.A. Microwaves: Theory and Application in Material Processing IV; Eds, American Ceramic Society, Westerville, Ohio, 1997; p 357
[69]. Varma R.S. Green Chem., 1999, 1:43
[70]. Kappe C.O. Angew. Chem. Int. Ed. Engl., 2004, 43:6250
[71]. Kappe C.O., Pieber B., Dallinger D. Angew. Chem. Int. Ed., 2013, 52:1088
[72]. Nain S., Singh R., Ravichandran S. Adv. J. Chem. Sec. A., 2019, 2:94
[73]. Alkherraz A., Hashad O., Elsherif K. Prog. Chem. Biochem. Res., 2019, 2:99
[74]. Venkateswarlu M., Kumar M., Kamatala C.R., Venkanna P., Saiprakash P.K. Chem. Method., 2017, 1:87
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