Transformations of enaminones. A simple one-pot synthesis of imidazolone derivatives

Tetrahedron

Volumn 68, Issue 2, 2012, Pages 516-522

  Bezenšek, Jure ^a   Grošelj, Uroš ^a   Stare, Katarina ^a   Svete, Jurij ^a   Stanovnik, Branko ^a  

^a UNIVERSITY OF LJUBLJANA   (Slovenia)

Author keywords

Enaminones; Imidazolones; Michael additions; One pot synthesis

Indexed keywords

2 [4 BENZOYL 3 [(ETHOXYCARBONYL)AMINO]2 OXO 2,3 DIHYDRO 1H IMIDAZOL 1 YL]PROPANOIC ACID; DIETHYL [3,30 (1,2 PHENYLENE)BIS(5 BENZOYL 2 OXO 2,3 DIHYDRO 1H IMIDAZOLE 3,1 DIYL)]DICARBAMATE; ETHYL (5 BENZOYL 2 OXO 3 (3 TOLYL) 2,3 DIHYDRO 1H IMIDAZOL 1 YL)CARBAMATE; ETHYL (5 BENZOYL 2 OXO 3 (4 TOLYL) 2,3 DIHYDRO 1H IMIDAZOL 1 YL)CARBAMATE; ETHYL (5 BENZOYL 2 OXO 3 PHENYL 2,3 DIHYDRO 1H IMIDAZOL 1 YL)CARBAMATE; ETHYL (5 BENZOYL 2 OXO 3 PROPYL 2,3 DIHYDRO 1H IMIDAZOL 1 YL)CARBAMATE; ETHYL (5 BENZOYL 2 OXO3 (PROP 2 YN 1 YL) 2,3 DIHYDRO 1H IMIDAZOL 1 YL)CARBAMATE; ETHYL (5 BENZOYL 3 (4 METHOXYPHENYL) 2 OXO 2,3 DIHYDRO 1H IMIDAZOL 1 YL)CARBAMATE; ETHYL (5 BENZOYL 3 BENZYL 2 OXO 2,3 DIHYDRO 1H IMIDAZOL 1 YL)CARBAMATE; ETHYL [5 BENZOYL 2 OXO 3 (PYRAZIN 2 YL) 2,3 DIHYDRO 1H IMIDAZOL 1 YL]CARBAMATE; ETHYL [5 BENZOYL 2 OXO 3 (PYRIDIN 2 YL) 2,3 DIHYDRO 1H IMIDAZOL 1 YL]CARBAMATE; ETHYL [5 BENZOYL 3 (3 NITROPHENYL) 2 OXO 2,3 DIHYDRO 1H IMIDAZOL 1 YL]CARBAMATE; ETHYL [5 BENZOYL 3 (4 BROMOPHENYL) 2 OXO 2,3 DIHYDRO 1H IMIDAZOL 1 YL]CARBAMATE; ETHYL [5 BENZOYL 3 (4 NITROPHENYL) 2 OXO 2,3 DIHYDRO 1H IMIDAZOL 1 YL]CARBAMATE; IMIDAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CYCLIZATION; DRUG STRUCTURE; DRUG TRANSFORMATION; MICHAEL ADDITION; ONE POT SYNTHESIS; PRIORITY JOURNAL;

EID: 82955163246     PISSN: 00404020     EISSN: 14645416     Source Type: Journal    
DOI: 10.1016/j.tet.2011.11.013     Document Type: Article

References (50)

1. A.V. Chebanov, S.M. Desenko, and T.W. Gurley Azaheterocycles Based on α,β-Unsaturated Carbonyl 2008 Springer Berlin
2. Z. Jin Nat. Prod. Rep. 26 2009 382
3. L. De Luca Curr. Med. Chem. 13 2006 1
4. B.M.J.M. Suijkerbuijk, I. Niculescu-Duvaz, C. Gaulon, H.P. Dijkstra, D. Niculescu-Duvaz, D. Menard, A. Zambon, A. Nourry, L. Davies, H.A. Manne, F. Friedlos, L.M. Ogilvie, D. Hedley, F. Lopes, N.P.U. Preece, J. Moreno-Farre, F.I. Raynaud, R. Kirk, S. Whittaker, R. Marais, and C.J. Springer J. Med. Chem. 53 2010 2741
5. P.E. Finke, L.C. Meurer, D.A. Levorse, S.G. Mills, M. MacCoss, S. Sadowski, M.A. Cascieri, K.-L. Tsao, G.G. Chicchi, J.M. Metzger, and D.E. MacIntyre Bioorg. Med. Chem. Lett. 16 2006 4497
6. R.W. Carling, K.W. Moore, C.R. Moyes, E.A. Jones, K. Bonner, F. Emms, R. Marwood, S. Patel, S. Patel, A.E. Fletcher, M. Beer, B. Sohal, A. Pike, and P.D. Leeson J. Med. Chem. 42 1999 2706
7. For a review see: P.J. De Clercq Chem. Rev. 97 1997 1755
8. A.C.B. Sosa, K. Yakushijin, and D.A. Horne Org. Lett. 2 2000 3443
9. A.C.B. Sosa, K. Yakushijin, and D.A. Horne J. Org. Chem. 67 2002 4498
10. P.J. Dransfield, A.S. Dilley, S. Wang, and D. Romo Tetrahedron 62 2006 5223
11. L. Selič, R. Jakše, K. Lampič, L. Golič, S. Golič-Grdadolnik, and B. Stanovnik Helv. Chim. Acta 83 2000 2802
12. P.B. Koswatta, R. Sivappa, H.V.R. Dias, and C.J. Lovely Synthesis 2009 2970
13. M.R. Grimmet Product Class 3: Imidazoles in Science of Synthesis Vol 12 2006 Georg Thieme Stuttgart 325 528
14. Grimmet, M. R. Imidazoles, in Comprehensive Heterocyclic Chemistry II; Katritzky, A.; Rees, C. W.; Scriven, E. F. V. Eds.; Elsevier, Vol. 3, pp. 77-220
15. Xi, N.; Huang, Q.; Liu, L. Imidazoles, in Comprehensive Heterocyclic Chemistry III; Katritzky, A.; Ramsden, C. A.; Scriven, E. F. V.; Taylor, R. J. K. Eds.; Elsevier, Vol. 4, pp. 143-362.
16. M. Debdab, S. Renault, S. Eid, O. Lozach, L. Meijer, F. Carreaux, and J.P. Bazureau Heterocycles 78 2009 1191
17. G. Brasche, and S.L. Buchwald Angew. Chem., Int. Ed. 47 2008 1932
18. G. Abbiati, A. Arcadi, V. Canevari, and E. Rossi Tetrahedron Lett. 48 2007 8491
19. J.C. Yoburn, and S. Baskaran Org. Lett. 7 2005 3801
20. O.A. Attanasi, G. Giorgi, G. Favi, P. Filippone, S. Lillini, F.R. Perrulli, and S. Santeusanio Synlett 2007 1691
21. D. Ma, and Q. Cai Acc. Chem. Res. 41 2008 1450
22. K. Kunz, U. Scholz, and D. Ganzer Synlett 2003 2428
23. G. Evano, N. Blanchard, and M. Toumi Chem. Rev. 108 2008 3054
24. F. Monnier, and M. Taillefer Angew. Chem., Int. Ed. 48 2009 6954 and references cited therein
25. X. Gong, H. Yang, H. Liu, Y. Jiang, Y. Zhao, and H. Fu Org. Lett. 12 2010 3128
26. R. Schnettler, R.C. Dage, and J.M. Grisar J. Med. Chem. 25 1982 1477
27. P.A. Innes, R.S. Frazer, P.D. Booker, E. Allsop, C. Kirton, J. Lockie, and R. Franks Br. J. Anaesth. 72 1994 77
28. P.D. Booker, S. Gibbons, J.I.M. Stewart, A. Selby, E. Wilson-Smith, and M. Pozzi Br. J. Anaesth. 85 2000 205
29. P. Ruef, E. Craciun, F. Altfelder, C. Simon, D. Frommhold, L. Koch, and J. Poeschl Clin. Hemorheol. Microcirc. 45 2010 301
30. B. Stanovnik J. Heterocycl. Chem. 36 1999 1581
31. B. Stanovnik, and J. Svete Synlett 2000 1077
32. B. Stanovnik, and J. Svete O.A. Attanasi, D. Spinelli, Targets in Heterocyclic Systems. Synthesis, Reactions and Properties Vol. 3 2000 Italian Society of Chemistry Rome 105
33. B. Stanovnik, and J. Svete Chem. Rev. 104 2004 2433
34. S. Strah, B. Stanovnik, and S. Golič Grdadolnik J. Heterocycl. Chem. 34 1997 263
35. U. Grošelj, D. Bevk, R. Jakše, S. Rečnik, A. Meden, B. Stanovnik, and J. Svete Tetrahedron 61 2005 3991
36. L. Kralj, A. Hvala, J. Svete, L. Golič, and B. Stanovnik J. Heterocycl. Chem. 34 1997 247
37. L. Selič, and B. Stanovnik Helv. Chim. Acta 81 1998 1634
38. L. Selič, and B. Stanovnik Tetrahedron 57 2001 3159
39. R. Jakše, J. Svete, and B. Stanovnik Tetrahedron 60 2004 4601
40. Z. Časar, D. Bevk, J. Svete, and B. Stanovnik Tetrahedron 61 2005 7508
41. J. Wagger, U. Grošelj, J. Svete, and B. Stanovnik Synlett 2010 1197 and references cited therein
42. U. Uršič, U. Grošelj, A. Meden, J. Svete, and B. Stanovnik Tetrahedron Lett. 49 2008 3775
43. U. Uršič, J. Svete, and B. Stanovnik Tetrahedron 64 2008 9937
44. U. Uršič, U. Grošelj, A. Meden, J. Svete, and B. Stanovnik Helv. Chim. Acta 92 2009 481
45. J. Bezenšek, T. Koleša, U. Grošelj, A. Meden, K. Stare, J. Svete, and B. Stanovnik Curr. Org. Chem. 15 2011 2530
46. Collect softwar; Nonius, B. V. Ed.; Delft, The Netherlands, 1998.
47. Z. Otwinowski, and W. Minor Methods Enzymol. 276 1997 307
48. A. Altomare, M.C. Burla, M. Camalli, G.L. Cascarano, C. Giacovazzo, A. Guagliardi, A.G.G. Moliterni, G. Polidori, and R. Spagna J. Appl. Crystallogr. 32 1999 115
49. S.R. Hall, G.S.D. King, and J.M. Stewart The Xtal3.4 User's Manual 1995 University of Western Australia Lamb/Perth
50. Burnett, M. N.; Johnson, C. K. In ORTEP-III: Oak Ridge Thermal Ellipsoid Plot Program for Crystal Structure Illustrations, Oak Ridge National Laboratory Report ORNL-6895, 1996.