[KSCI] Korea Science Citation Index Service

http://dx.doi.org/10.5012/bkcs.2008.29.9.1752

Synthesis of 3,4-Dihydropyrimidin-2(1H)-ones Using HClO₄-SiO₂ as a Heterogeneous and Recyclable Catalyst

Maheswara, Muchchintala (Department of Advanced Materials for Information and Display, Pusan National University)
Oh, Sang-Hyun (Department of Advanced Materials for Information and Display, Pusan National University)
Kim, Ke-Tack (Korea Electrotechnology Research Institute)
Do, Jung-Yun (Department of Advanced Materials for Information and Display, Pusan National University)

Publication Information

Bulletin of the Korean Chemical Society / v.29, no.9, 2008 , pp. 1752-1754 More about this Journal

Abstract

A simple and efficient synthesis of 3,4-dihydropyrimidinones or thiones is described, using silica-supported perchloric acid ( $HClO_4-SiO_2$ ) as a heterogeneous catalyst from an aldehyde, $\beta$ -dicarbonyl compound, and urea or thiourea under solvent-free conditions. Compared to the classical Biginelli reactions, this method consistently has the advantage of high yields, short reaction time, easy separation, and tolerance towards various functional groups.

Keywords

Dihydropyrimidinones; Dihydropyrimidinthiones; HClO₄-SiO₂; Silica-supported catalyst

Citations & Related Records

Times Cited By KSCI : 2 (Citation Analysis)
Times Cited By Web Of Science : 8 (Related Records In Web of Science)
Times Cited By SCOPUS : 10

1	Mukinsty, D. W.; Reading, E. H. J. Franklin Inst. 1944, 237, 422 DOI ScienceOn
2	Kato, T. Jpn. Kokai Tokkyo Koho JP 1984, 59, 974 [Chem. Abstr. 102 (1985), 132067]
3	Sadanandam, Y. S.; Shetty, M. M.; Diwan, P. V. Eur. J. Med. Chem. 1992, 27, 87 DOI ScienceOn
4	Bozing, D.; Benko, P.; Petcoz, L.; Szeesey, M.; Toempe, P.; Gigler, G.; Gacsalyi, I.; Gyertyan I. (EGIS Gyogyszergyar) Eur. Pat. Appl. E P 409, 233, 1991 (Chem. Abstr. 1991, 114, 247302z)
5	Overman, L. E.; Rabinowitz, M. H.; Renhowe, P. A. J. Am. Chem. Soc. 1995, 117, 2657 DOI ScienceOn
6	Patil, A. D.; Kumar, N. V.; Kokke, W. C.; Bean, M. F.; Freyer, A. J.; Brosse, C. D.; Mai, S.; Truneh, A.; Faulkner, D. J.; Carte, B.; Breen, A. L.; Hertzberg, R. P.; Johnson, R. K.; Westly, J. W.; Ports, B. C. M. J. Org. Chem. 1995, 60, 1182 DOI ScienceOn
7	Kappe, C. O.; Falsone, S. F. Synlett 1998, 718
8	Bigi, F.; Carloni, S.; Frullanti, B.; Maggi, R.; Sartori, G. Tetrahedron Lett. 1999, 40, 3465 DOI ScienceOn
9	Lu, J.; Ma, H. Synlett 2000, 63
10	Hu, E. H.; Sidler, D. R.; Dolling, U. H. J. Org. Chem. 1998, 63, 3454 DOI ScienceOn
11	Lu, J.; Bai, Y.; Wang, Z.; Yang, B.; Ma, H. Tetrahedron Lett. 2000, 41, 9075 DOI ScienceOn
12	Narasaiah, A. V.; Basakar, A.; Nagaiah, K. Synthesis 2004, 8, 1253
13	Ma, Y.; Qian, C.; Wang, L.; Yang, M. J. Org. Chem. 2000, 65, 3864 DOI ScienceOn
14	Bose, D. S.; Kumar, R. K.; Fatima, L. Synlett 2004, 279
15	Chakrabarti, A. K.; Gulhane, R. Chem. Commun. 2003, 1896
16	Su, W.; Li, J.; Zheng, Z.; Shen, Y. Tetrahedron Lett. 2005, 46, 6037 DOI ScienceOn
17	Das, B.; Laxminarayana, K.; Ravikanth, B. J. Mol. Cat. A 2007, 271, 131 DOI ScienceOn
18	Kappe, C. O. Bioorg. Med. Chem. Lett. 2000, 10, 49 DOI ScienceOn
19	Das, B.; Venkateswarlu, K.; Majhi, A.; Reddy, M. R.; Reddy, K. N.; Rao, Y. K.; Ravikumar, K.; Sridhar, B. J. Mol. Cat. A 2006, 246, 276 DOI ScienceOn
20	Li, J. T.; Jun, J. H.; Yang, J. H.; Li, T. S. Ultrasonic 2003, 10, 119
21	Reddy, Y. T.; Reddy, P. N.; Kumar, B. S.; Rao, G. V. P.; Rajitha, B. Indian J. Chem. 2005, 44B, 1304
22	Nasr-Esfahani, M.; Khosropour, A. R. Bull. Korean Chem. Soc. 2005, 26(9), 1331 DOI ScienceOn
23	Matsuda, T.; Hirao, I. Nippon Kagaku Zasshi 1965, 86, 1195
24	Atwal, K. S.; Rovnyak, G. C.; O'Reilly, B. C.; Schwartz, J. J. Org. Chem. 1989, 54, 5898 DOI
25	Kappe, C. O.; Fabian, W. M. F.; Semones, M. A. Tetrahedron 1997, 53, 2803 DOI ScienceOn
26	Kim, K. W.; Lee, H. J.; Kim, C. G.; Park, M.; Kwon, T. W. Bull. Korean Chem. Soc. 2008, 29(3), 604 DOI ScienceOn
27	Ranu, B. C.; Hazra, A.; Jana, U. J. Org. Chem. 2000, 65, 6270 DOI ScienceOn
28	Stefani, H. A.; Gatti, P. M. Synth. Commun. 2000, 30, 2165 DOI ScienceOn
29	Gohain, M.; Prajapati, D.; Sandhu, J. S. Synlett 2004, 235
30	Studer, A.; Jeger, P.; Wip, P.; Curran, D. P. J. Org. Chem. 1997, 62, 2917 DOI ScienceOn

12	Kulsum Khan. (2015) Monatshefte für Chemie - Chemical Monthly MCM-41 supported perchloric acid for efficient synthesis of 3,4-dihydropyrimidin-2-(1H)-ones via Biginelli reaction / 146 (12) , 2097
14	(2017) New Journal of Chemistry 1,3,5-Tris(2-hydroxyethyl)isocyanurate functionalized graphene oxide: a novel and efficient nanocatalyst for the one-pot synthesis of 3,4-dihydropyrimidin-2(1H)-ones / 41 (14) , 6893
5	Mehrnoush Kangan. (2017) Journal of the Chinese Chemical Society Efficient Synthesis of 5-Carboxanilide-Dihydropyrimidinones Using Cobalt(II) Nitrate Hexahydrate / 64 (5) , 481
4	(2010) Molecules Ultrasound-Assisted Synthesis of Novel 4-(2-Phenyl-1,2,3-Triazol-4-yl)-3,4-Dihydropyrimidin-2(1H)-(Thio)ones Catalyzed by Sm(ClO4)3 / 15 (4) , 2087
8	(2016) Chemické zvesti Solvent-free synthesis of 6-unsubstituted dihydropyrimidinones using 2-pyrrolidonium bisulphate as efficient catalyst / 70 (8) , 1126
5	Muchchintala Maheswara. (2009) ChemInform as a Heterogeneous and Recyclable Catalyst. / 40 (5)
1	(2008) Molecular diversity A chemical placebo: NaCl as an effective, cheapest, non-acidic and greener catalyst for Biginelli-type 3,4-dihydropyrimidin-2(1H)-ones (-thiones) synthesis / 13 (1) , 5
2	(2008) Bulletin of the Korean Chemical Society Nickel Nanoparticles: An Ecofriendly and Reusable Catalyst for the Synthesis of 3,4-Dihydropyrimidine-2(1H)-ones via Biginelli Reaction / 31 (2) , 351
3	(2008) Bulletin of the Korean Chemical Society Thickness Control of Biomimetic Silica Thin Films: Grafting Density of Poly(2-(dimethylamino)ethyl methacrylate) Templates / 31 (3) , 753
16	Chennan Ramalingan. (2008) Tetrahedron A piperidinium triflate catalyzed Biginelli reaction / 66 (16) , 2987
3	(2019) ACS combinatorial science Biginelli Reaction: Polymer Supported Catalytic Approaches / 21 (3) , 105
28	(2008) ChemistrySelect HClO <SUB>4</SUB> ‐Al <SUB>2</SUB> O <SUB>3</SUB> as a Prominent Catalyst in the Synthesis of 3,4‐Dihydropyrimidin‐2(1 H )‐ones/thiones under Environmentally Friendly Solve / 5 (28) , 8604

1	/ Molecular Diversity
2	/ Tetrahedron
3	/ Indian Drugs
4	/ Bulletin of the Korean Chemical Society
5	/ Journal of Organic Chemistry
6	/ Arkivoc
7	/ Molecules
8	/ Bulletin of the Korean Chemical Society
9	/ Chemical Reviews

1	Nickel Nanoparticles: An Ecofriendly and Reusable Catalyst for the Synthesis of 3,4-Dihydropyrimidine-2(1H)-ones via Biginelli Reaction / [Sapkal, Suryakant B.;Shelke, Kiran F.;Shingate, Bapurao B.;Shingare, Murlidhar S.;] / Bulletin of the Korean Chemical Society
2	Thickness Control of Biomimetic Silica Thin Films: Grafting Density of Poly(2-(dimethylamino)ethyl methacrylate) Templates / [Yang, Sung-Ho;Choi, In-Sung S.;] / Bulletin of the Korean Chemical Society

KSCI

Synthesis of 3,4-Dihydropyrimidin-2(1H)-ones Using HClO4-SiO2 as a Heterogeneous and Recyclable Catalyst

Synthesis of 3,4-Dihydropyrimidin-2(1H)-ones Using HClO₄-SiO₂ as a Heterogeneous and Recyclable Catalyst