Development and efficient 1-glycyl-3-methyl imidazolium chloride-copper(II) complex catalyzed highly enantioselective synthesis of 3, 4-dihydropyrimidin- 2(1H)-ones

Journal of Organometallic Chemistry

Volumn 723, Issue , 2013, Pages 154-162

  Karthikeyan, Parasuraman ^a   Aswar, Sachin Arunrao ^a   Muskawar, Prashant Narayan ^a   Bhagat, Pundlik Rambhau ^a   Senthil Kumar, S ^a  

^a VIT UNIVERSITY   (India)

Author keywords

3, 4 dihydropyrimidin 2(1H) one; Amino acid; Copper complex; Ionic liquid

Indexed keywords

3, 4-DIHYDROPYRIMIDIN-2(1H)-ONE; AFM; BIGINELLI REACTION; C-C BONDS; CATALYST RECYCLING; COPPER COMPLEXES; ENANTIOSELECTIVE; ENANTIOSELECTIVE SYNTHESIS; ENVIRONMENTALLY BENIGN; HETEROGENEOUS CATALYST; HIGH YIELD; HYDROPHOBIC GROUPS; IMIDAZOLIUM; ORGANOCATALYSTS; POWDER XRD; PRODUCT ISOLATION; SOLVENT FREE CONDITIONS; SPECTROSCOPIC EVIDENCE; SUPPORTED PALLADIUM;

ALDEHYDES; AMINO ACIDS; CATALYSTS; COPPER; COPPER COMPOUNDS; ENANTIOSELECTIVITY; IONIC LIQUIDS; PALLADIUM COMPOUNDS;

CHLORINE COMPOUNDS;

EID: 84868671402     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jorganchem.2012.06.022     Document Type: Article

References (43)

1. P. Biginelli Gazz. Chim. Ital 23 1893 360 416
2. A. Dondoni, and A. Massi Acc. Chem. Res. 39 2006 451 463
3. Z.D. Aron, and L.E. Overman Chem. Commun. 2004 253 265
4. T. Welton Chem. Rev. 99 1999 2071 2084
5. R. Rajgopal, D.V. Jarikote, R.J. Lahoti, D. Thomas, and K.V. Srinivasan Tetrahedron Lett. 44 2003 1815 1817
6. D.E. Siyutkin, A.S. Kucherenko, and S.G. Zlotin Tetrahedron 65 2009 1366 1372
7. Y. Yang, Y. Zhang, S. Hao, and Q. Kan Chem. Eng. J. 171 2011 1356 1366
8. Y. Yang, J. Guan, P. Qiu, and Q. Kan Appl. Surface. Sci. 256 2010 3346 3351
9. S. Jana, S. Bhunia, B. Dutta, and S. Koner Appl. Catal. A: Gen. 392 2011 225 232
10. A. Shaabani, A. Bazgir, and F. Teimouri Tetrahedron Lett. 44 2003 857 859
11. M.V. Kirillova, A.M. Kirillov, D. Mandelli, W.A. Carvalho, A.J.L. Pombeiro, and G.B. Shulpin J. Catal. 272 2010 9 17
12. R.R. Fernandes, J. Lasri, M.F.C. Guedes da Silva, J.A.L. da Silva, J.J.R. Frausto da Silva, and A.J.L. Pombeiro Appl. Catal. A: Gen. 402 2011 110 120
13. S.M. Islam, A.S. Roy, P. Mondal, M. Mubarak, S. Mondal, D. Hossain, S. Banerjee, and S.C. Santra J. Mol. Catal. A: Chem. 336 2011 106 114
14. M.V. Kirillova, Y.N. Kozlov, L.S. Shulpina, O.Y. Lyakin, A.M. Kirillov, E.P. Talsi, A.J.L. Pombeiro, and G.B. Shulpin J. Catal. 268 2009 26 38
15. A.M. Kirillov, M.V. Kirillova, L.S. Shulpina, P.J. Figiel, K.R. Gruenwald, M.F.C. Guedes da Silva, M. Haukkad, A.J.L. Pombeiro, and G.B. Shulpine J. Mol. Catal. A: Chem. 350 2011 26 34
16. M.V. Kirillov, A.M. Kirillov, and A.J.L. Pombeiro Appl. Catal. A: Gen. 401 2011 106 113
17. W.S. Lee, C.T. Yeung, K.C. Sham, W.T. Wong, and H.L. Kwong Polyhedron 30 2011 178 186
18. H.B. Zhu, Z.Y. Dai, W. Huang, K. Cui, S.H. Gou, and C.J. Zhu Polyhedron 23 2004 1131 1137
19. M. Sedlak, P. Drabina, R. Keder, J. Hanusek, I. Csarova, and A. Ruzick J. Organomet. Chem. 691 2006 2623 2630
20. S.S. Chavan, S.K. Sawant, V.A. Sawant, and G.K. Lahiri Inorg. Chem. Commun. 14 2011 1373 1376
21. S.K. Sawant, G.A. Gaikwad, V.A. Sawant, B.A. Yamgar, and S.S. Chavan Inorg. Chem. Comm. 12 2009 632 635
22. M. Konig, L.M. Reith, U. Monkowius, G. Knor, K. Bretterbauer, and W. Schoefberger Tetrahedron 67 2011 4243 4252
23. B.S. Zhang, C. Wang, J.F. Gong, and M.P. Song J. Organomet. Chem. 694 2009 2555 2561
24. S.M. Islam, P. Mondal, A. Singh Roy, S. Mondal, and D. Hossain Tetrahedron Lett. 51 2010 2067 2070
25. Y. Huang, F. Yang, and C. Zhu J. Am. Chem. Soc. 127 2005 16386 16387
26. X.-H. Chen, X.-Y. Xu, H. Liu, L.-F. Cun, and L.-Z. Gong J. Am. Chem. Soc. 128 2006 14802 14803
27. Y. Wang, H. Yang, J. Yu, Z. Miao, and R. Chena Adv. Synth. Catal. 351 2009 3057 3062
28. N. Li, X.-H. Chen, J. Song, S.-W. Luo, W. Fan, and L.-Z. Gong J. Am. Chem. Soc. 131 2009 15301 15310
29. Y.-F. Cai, H.-M. Yang, L. Li, K.-Z. Jiang, G.-Q. Lai, J.-X. Jiang, and L.-W. Xu J. Org. Chem. 2010 4986 4990
30. R. Sebest, I. Kmentov, and S. Tom Green. Chem. 10 2008 484 496
31. W.S. Miao, and T.H. Chan Adv. Synth. Catal. 348 2006 1711 1718
32. M. Lombardo, F. Pasi, S. Easwar, and C. Trombini Adv. Synth. Catal. 349 2007 2061 2065
33. P. Karthikeyan, P.N. Muskawar, S.A. Aswar, P.R. Bhagat, and S.K. Sythana J. Mol. Catal. A: Chem. 358 2012 112 120
34. M. Lombardo, F. Pasi, S. Easwar, and C. Trombini Synlett 2008 2471 2474
35. M. Lombardo, S. Easwar, A. DeMarco, F. Pasi, and C. Trombini Org. Biomol. Chem. 6 2008 4224 4229
36. D.S. Tarbell, Y. Yamamoto, and B.M. Pope Proc. Acad. Sci. U S A 69 1972 730 732
37. L. Moroder, S. Hallett, E. Wunsch, O. Keller, G. Wersin, and Z. Hoppe Seyler's Physiol. Chem. 357 1976 1651
38. J.R. Rachele J. Org. Chem. 28 1963 2898
39. D. Ben-ishai, and A. Berger J. Org. Chem. 17 1952 1564 1570
40. D. Ben-ishai J. Org. Chem. 19 1954 62 66
41. M. Bodanszky, and V. du Vigneaud J. Am. Chem. Soc. 81 1959 5688 5691
42. X. Hu, J. Mao, Y. Sun, H. Chen, and H. Li Catal. Commun. 10 2009 1908 1912
43. A.A. El-Sherif Inorg. Chim. Acta 362 2009 4991 5000