One pot solid phase synthesis of 2-substituted 2,3-dihydropyridin-4(1H)- ones on Rinkamide-resin

Tetrahedron

Volumn 61, Issue 1, 2005, Pages 205-211

  Sax, Michael ^a   Berning, Stefanie ^a   Wünsch, Bernhard ^a  

^a UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

Dihydropyridones; Hetero Diels Alder reaction; Parallel synthesis; Solid phase synthesis

Indexed keywords

2 (2 BROMOPHENYL) 2,3 DIHYDROPYRIDIN 4(1H) ONE; 2 (2 METHYLPROPYL) 2,3 DIHYDROPYRIDIN 4(1H) ONE; 2 (4 NITROPHENYL) 2,3 DIHYDROPYRIDIN 4(1H) ONE; 2 (FURAN 2 YL) 2,3 DIHYDROPYRIDIN 4(1H) ONE; 2 (THIOPHEN 2 YL) 2,3 DIHYDROPYRIDIN 4(1H) ONE; 2 BUTYL 2,3 DIHYDROPYRIDIN 4(1H) ONE; 2 CYCLOHEXYL 2,3 DIHYDROPYRIDIN 4(1H) ONE; 2 ISOPROPYL 2,3 DIHYDROPYRIDIN 4(1H) ONE; 2 PHENYL 2,3 DIHYDROPYRIDIN 4(1H) ONE; 2 TERT BUTYL 2,3 DIHYDROPYRIDIN 4(1H) ONE; 2,3 DIHYDRO 2,2' BIPYRIDIN 4(1H) ONE; ETHYL 2 METHYL 4 OXO 1,2,3,4 TETRAHYDROPYRIDINE 2 CARBOXYLATE; PYRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DIELS ALDER REACTION; DRUG SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS; SOLID; SUBSTITUTION REACTION;

BETULACEAE;

EID: 9644260412     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.10.031     Document Type: Article

References (32)

1. A. Thurkauf, M.V. Mattson, S. Richardson, S. Mirsadeghi, P.L. Ornstein, E.A. Harrison Jr., K.C. Rice, A.E. Jacobson, and J.A. Monn J. Med. Chem. 35 1992 1323 1329
2. S. Nara, R. Tanaka, J. Eishima, M. Hara, Y. Takahashi, S. Otaki, R.J. Foglesong, P.F. Hughes, S. Turkington, and Y. Kanda J. Med. Chem. 46 2003 2467 2473
3. H. Bhagwatheeswaran, S.P. Gaur, and P.C. Jain Synth. Commun. 1976 615 616
4. M.C. Desai, P.F. Thadeio, and S.L. Lefkowitz Tetrahedron Lett. 34 1993 5831 5834
5. M.C. Desai, and S.L. Lefkowitz Bioorg. Med. Chem. Lett. 3 1993 2083 2086
6. T. Rosen, T.F. Seeger, S. McLean, M.C. Desai, K.J. Guarino, D. Bryce, K. Pratt, and J. Heym J. Med. Chem. 36 1993 3197 3201
7. A. Barco, S. Benetti, C. De Risi, P. Marchetti, G.P. Pollini, and V. Zanirato Tetrahedron Lett. 39 1998 1973 1976
8. A. Barco, S. Benetti, C. De Risi, P. Marchetti, G.P. Pollini, and V. Zanirato Tetrahedron Lett. 39 1998 7591 7594
9. For reviews concerning HDA-reactions see: (a) K.A. Jørgensen Angew. Chem. 112 2000 3702 3733
10. P. Buonora, J.-C. Olsen, and T. Oh Tetrahedron 57 2001 6099 6138
11. S. Danishefsky Acc. Chem. Res. 14 1981 400 406
12. Y. Wang, and S.R. Wilson Tetrahedron Lett. 38 1997 4021 4024
13. J. Barluenga, C. Mateos, F. Aznar, and C. Valdés Org. Lett. 4 2002 3667 3670
14. C. Chen, I.A. McDonald, and B. Munoz Tetrahedron Lett. 39 1998 217 220
15. G.C. Look, M.M. Murphy, D.A. Campbell, and M.A. Gallop Tetrahedron Lett. 36 1995 2937 2940
16. R. Badorrey, C. Cativiela, M.D. Díaz-de-Villegas, and J.A. Gálvez Tetrahedron Lett. 38 1997 2547 2550
17. J. Barluenga, C. Mateos, F. Aznar, and C. Valdés Organic Lett. 4 2002 1971 1974
18. S. Hermitage, D.A. Jay, and A. Whiting Tetrahedron Lett. 43 2002 9633 9636
19. J.T. Kuethe, I.W. Davies, P.G. Dormer, R.A. Reamer, D.J. Mathre, and P.J. Reider Tetrahedron Lett. 43 2002 29 32
20. J.T. Kuethe, A. Wong, I.W. Davies, and P.J. Reider Tetrahedron Lett. 43 2002 3871 3874
21. K. Hattori, and H. Yamamoto J. Org. Chem. 57 1992 3264 3265
22. K. Hattori, and H. Yamamoto Tetrahedron 49 1993 1749 1760
23. N.S. Josephson, M.L. Snapper, and A.H. Hoveyda J. Am. Chem. Soc. 125 2003 4018 4019
24. R. Badorrey, C. Cativiela, M.D. Díaz-de-Villegas, and J.A. Gálvez Tetrahedron 58 2002 341 354
25. Y. Yuan, X. Li, and K. Ding Org. Lett. 4 2002 3309 3311
26. C. Loncaric, K. Manabe, and S. Kobayashi Chem. Commun. 2003 574 575
27. Y. Huang, and V.H. Rawal J. Am. Chem. Soc. 124 2002 9662 9663
28. 2 at -25°C, dark (proved by NMR-analysis; purity ≥95% after 21 days).
29. W.C. Still, M. Kahn, and A. Mitra J. Org. Chem. 43 1978 2325 2923
30. L. Hansson, and R. Carlson Acta Chem. Scand. 43 1989 188 192
31. P.S. Watson, B. Jiang, and B. Scott Org. Lett. 2 2000 3679 3681
32. D.L. Comins, S.P. Joseph, and R.R. Goehring J. Am. Chem. Soc. 116 1994 4719 4728