Lewis acid promoted imino Diels-Alder reactions of 5-dienyl pyrimidinones with N-aryl/naphthyl imines: synthesis of novel quinoline/benzoquinoline derivatives

Tetrahedron

Volumn 64, Issue 13, 2008, Pages 3017-3024

  Bhargava, Gaurav ^a   Mohan, Chander ^a   Mahajan, Mohinder P ^a  

^a GURU NANAK DEV UNIVERSITY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

5 [2 (2 (4 CHLORO PHENYL) 6 METHOXY QUINOLIN 4 YL) VINYL] 2,3 DIPHENYL 3H PYRIMIDIN 4 ONE; 5 [2 (2 (4 CHLORO PHENYL) 6 METHOXY QUINOLIN 4 YL) VINYL] 6 METHYL 2,3 DIPHENYL 3H PYRIMIDIN 4 ONE; 5 [2 (2 (4 CHLORO PHENYL) 6 METHOXY QUINOLIN 4 YL) VINYL] 6 MORPHOLIN 4 YL 2,3 DIPHENYL 3H PYRIMIDIN 4 ONE; 5 [2 (6 METHOXY 2 (2 METHOXY PHENYL) QUINOLIN 4 YL) VINYL] 2,3 DIPHENYL 3H PYRIMIDIN 4 ONE; 5 [2 (6 METHOXY 2 (4 METHOXY PHENYL) QUINOLIN 4 YL) VINYL] 6 METHYL 2,3 DIPHENYL 3H PYRIMIDIN 4 ONE; 5 [2 (6 METHOXY 2 (4 METHOXY PHENYL) QUINOLIN 4 YL) VINYL] 6 MORPHOLIN 4 YL 2,3 DIPHENYL 3H PYRIMIDIN 4 ONE; 5 [2 (6 METHOXY 2 PHENYL QUINOLIN 4 YL) VINYL] 2,3 DIPHENYL 3H PYRIMIDIN 4 ONE; 5 [2 (6 METHOXY 2 PHENYL QUINOLIN 4 YL) VINYL] 6 METHYL 2,3 DIPHENYL 3H PYRIMIDIN 4 ONE; 5 [2 (8 METHOXY 2 PHENYL QUINOLIN 4 YL) VINYL] 2,3 DIPHENYL 3H PYRIMIDIN 4 ONE; 5 [2 (8 METHOXY 2 PHENYL QUINOLIN 4 YL) VINYL] 6 METHYL 2,3 DIPHENYL 3H PYRIMIDIN 4 ONE; 5 [2 (8 METHOXY 2 PHENYL QUINOLIN 4 YL) VINYL] 6 MORPHOLIN 4 YL 2,3 DIPHENYL 3H PYRIMIDIN 4 ONE; LEWIS ACID; PYRIMIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYST; DIELS ALDER REACTION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

ALNUS;

EID: 39149144482     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.01.041     Document Type: Article

References (50)

1. For leading references, see:
2. Daly J.W., and Spande T.F. In: Pelletier S.W. (Ed). Alkaloids: Chemical and Biological Perspectives Vol. 4 (1986), Wiley, New York, NY 1-254
3. Fodor G.B., and Colasanti B. In: Pelletier S.W. (Ed). Alkaloids: Chemical and Biological Perspectives Vol. 3 (1985), Wiley, New York, NY 1-91
4. Boger D., and Weinreb S.M. Hetero Diels-Alder Methodology in Organic Synthesis (1987), Academic, San Diego, CA Chapter 2, pp 34-70; Chapter 9, pp 239-299 and references therein
5. Boger D.L., and Patel M. In: Suschitzky H., and Scriven E.F.V. (Eds). Progress in Heterocyclic Chemistry (1989), Pergamon, New York, NY 1-30
6. Kametani T., and Hibino S. Adv. Heterocycl. Chem. 42 (1987) 246-333
7. For recent reviews see:
8. Buonora P., Olsen J.-C., and Oh T. Tetrahedron 57 (2001) 6099
9. Jørgensen K.A. Angew. Chem., Int. Ed. 39 (2000) 3558 and references cited therein
10. Orr R.K., and Calter M.A. Tetrahedron 59 (2003) 3545 and references cited therein
11. For recent examples see:
12. Takasu K., Shindoh N., Tokuyama H., and Ihara M. Tetrahedron 62 (2006) 11900
13. Manian R.D.R.S., Jayashankaran J., Ramesh R., and Raghunathan R. Tetrahedron Lett. 47 (2006) 7571
14. Yadav J.S., Reddy B.V.S., Kondaji G., Sowjanya S., and Nagaiah K. J. Mol. Catal. A: Chem. 258 (2006) 361
15. Prenzel A.H.G.P., Deppermann N., and Maison W. Org. Lett. 8 (2006) 1681
16. Zhou Y., Jia X., Li R., Liu Z., Liu Z., and Wu L. Tetrahedron Lett. 46 (2005) 8937
17. Rodrý'guez M., Ochoa M.E., Santillan R., Farfa'n N., and Barba V. J. Organomet. Chem. 690 (2005) 2975
18. Garcia A.-B., Valdes C., and Cabal M.-P. Tetrahedron Lett. 45 (2004) 4357
19. Danieli B., Lesma G., Passarella D., Piacenti P., Sacchetti A., Silvani A., and Virdis A. Tetrahedron Lett. 43 (2002) 7155
20. Tietze L.F., and Kettschau G. Top. Curr. Chem. 189 (1997) 1-120
21. Kobayashi S. Eur. J. Org. Chem. (1999) 15-27
22. Panunzio M., and Zarantonello P. Org. Process Res. Dev. 2 (1988) 49-59
23. Enders D., and Meyer O. Liebigs Ann. Chem. (1996) 1023-1035
24. Waldmann H. In: Waldman H. (Ed). Organic Synthesis Highlights II (1995), VCH, New York, NY 37-47
25. Waldmann H. Synthesis (1994) 535-551
26. Waldmann H., and Braun M. Gazz. Chim. Ital. 121 (1991) 277-284
27. Waldmann H. Synlett (1995) 133-141
28. Barluenga J., Joglar J., Gonzalez F.J., and Fustero S. Synlett (1990) 129-138
29. Parker D.T. In: Grieco P.A. (Ed). Organic Synthesis in Water Vol 2 (1998), Blackie Academic and Professional, London 47-81
30. Barluenga J., and Tomas M. Adv. Heterocycl. Chem. 57 (1993) 1-80
31. Kobayashi S., Ishitani H., and Nagayama S. Synthesis (1995) 1195-1202
32. Kobayashi S., and Nagayama S. J. Am. Chem. Soc. 118 (1996) 8977-8978
33. Szczech G.M., Furman P., Painter G.R., Barry D.W., Borroto-Esoda K., Grizzle T.B., Blum M.R., Sommadossi J.-P., Endoh R., Niwa T., Yamamoto M., and Moxham C. Antimicrob. Agents Chemother. 44 (2000) 123
34. Dieterle F., Müller-Hagedon S., Liebich H.M., and Gauglitz G. Artif. Intell. Med. 28 (2003) 265
35. Rowley D.C., Hansen M.S.T., Rhodes D., Striffer C.A., Ni H., McCammon J.A., Bushman F.D., and Fenical W. Bioorg. Med. Chem. 10 (2002) 3619
36. Molina P., Aller E., Lorenzo A., Lopez-Cremades P., Rioja I., Ubeda A., Terencio M.C., and Alcaraz M.J. J. Med. Chem. 44 (2001) 1011
37. Kumar A., Sinha S., and Chauhan P.M.S. Bioorg. Med. Chem. Lett. 12 (2002) 667
38. Bher J.-B., Gourlain T., Helimi A., and Guillerm G. Bioorg. Med. Chem. Lett. 13 (2003) 1713
39. De Koning H.P., Al-Salabi M.I., Cohen A.M., Coombs G.H., and Wastling J.M. Int. J. Parasitol. 33 (2003) 821
40. Hosni H.M., Basyouni W.M., and El-Nahas H.A. J. Chem. Res., Synop. (1999) 646
41. Botta M., Occhionero F., Nicoletti R., Mastromarino P., Conti C., Margini M., and Saladino J. Bioorg. Med. Chem. 9 (1999) 1925
42. Seeman P., Guan H.-C., Nobrega J., Jiwa D., Markstein R., Balk J.-H., Picetti R., Borrelli E., and Tol H.H.M.V. Synapse 25 (1997) 137
43. Elslager E.F., Short W.F., and Tendick H.F. J. Heterocycl. Chem. 5 (1968) 599
44. Bhargava G., Kumar V., and Mahajan M.P. Tetrahedron Lett. 48 (2007) 2365
45. Goel R.K., Kumar V., and Mahajan M.P. Bioorg. Med. Chem. Lett. 15 (2005) 2145
46. Bedi P.M.S., Kumar V., and Mahajan M.P. Bioorg. Med. Chem. Lett. 14 (2004) 5211
47. Goel R.K., Thind J.S., Bal C.S., Mahajan M.P., and Kulkarni S.K. Die Pharmazie (2005) 369-374
48. Bhargava G., Mahajan M.P., Saito T., Otani T., Kurashima M., and Sakai K. Eur. J. Org. Chem. (2005) 2397
49. Mohan C., Bhargava G., Pannu A.P.S., and Mahajan M.P. Tetrahedron Lett. 48 (2007) 1711
50. 3, dry dichloromethane was used as a solvent.