An efficient strategy for the construction of X-azatricyclo[m.n.0.0 a,b]alkanes by intramolecular [3 +2] cycloaddition of nonstabilized cyclic azomethine ylides

Arkivoc

Volumn 2001, Issue 8, 2001, Pages 83-94

  Pandey, Ganesh ^a   Sahoo, Akhila K ^a   Bagul, Trusar D ^a   Gadre, Smita R ^a  

^a NATIONAL CHEMICAL LABORATORY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ALKANE DERIVATIVE; ALKYL GROUP; AMINE; AZOMETHINE YLIDE; BENZENE; DOPAMINE TRANSPORTER; ETHYL 2 AZATRICYCLO[4.4.0.0 2,8 ]DECANE 7 CARBOXYLATE; ETHYL 2 AZATRICYCLO[5.4.0.0 2,9 ]UNDECANE 8 CARBOXYLATE; ETHYL 2 AZATRICYCLO[5.5.0.0 2,9 ]DODECANE 8 CARBOXYLATE; ETHYL 3 [2 [2,5 BIS(TRIMETHYLSILYL)TETRAHYDRO 1H PYRROLYLMETHYL]PHENYL] 2 PROPENOATE; ETHYL 3 [2 [2,6 BIS(TRIMETHYLSILYL)HEXAHYDRO 1 PYRIDINYLMETHYL]PHENYL] 2 PROPENOATE; ETHYL 6 [2,5 BIS(TRIMETHYLSILYL)TETRAHYDRO 1H 1 PYRROLYL] 2 HEXENOATE; ETHYL 6 [2,6 BIS(TRIMETHYLSILYL)HEXAHYDRO 1 PYRIDINYL] 2 HEXENOATE; ETHYL 7 [2,5 BIS(TRIMETHYLSILYL)TETRAHYDRO 1H 1 PYRROLYL] 2 HEPTANOATE; ETHYL 7 [2,6 BIS(TRIMETHYLSILYL)HEXAHYDRO 1 PYRIDINYL] 2 HEPTANOATE; ETHYL 7 AZATRICYCLO[5.4.0.0 3,8 ]UNDECANE 2 CARBOXYLATE; ETHYL 8 AZATETRACYCLO[8.4.0.0 2,7 .0 4,8 ]TETRADECA 1(10),11,13 TRIENE 3 CARBOXYLATE; ETHYL 9 AZATETRACYCLO[8.5.0.0 2,7 .0 9,14 ]PENTADECA 2(7),3,5 TRIENE 15 CARBOXYLATE; HETEROCYCLIC COMPOUND; OXIDIZING AGENT; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; CYCLIZATION; CYCLOADDITION; DESILYLATION; DRUG BINDING; DRUG SELECTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; ELECTRON; STRUCTURE ANALYSIS;

EID: 3242693562     PISSN: 14246376     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (60)

1. "The Alkaloids-Specialist Periodical Reports"; The Royal Society: London, 1983.
2. (a) Padwa, A. Angew. Chem., Int. Ed. Engl. 1976, 15, 123.
3. (b) Oppalzer, W. Angew. Chem., Int. Ed. Engl. 1977, 16, 10.
4. (c) Padwa, A. "1, 3- Dipolar Cycloaddition Chemistry." Wiley- Interscience, New York, 1984; Vol. 2, p 277.
5. Wade, P. A. Intramolecular 1, 3- Dipolar Cycloadditions In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Eds.; Pergamon: London, 1991; Vol. 4, p 1111.
6. Smith, R.; Livinghouse, T. J. Org. Chem. 1983, 48, 1554.
7. Westling, M.; Smith, R.; Livinghouse, T. J. Org. Chem. 1986, 51, 1159.
8. Wang, C. J.; Ripka, W. C.; Confalone, P. N. Tetrahedron Lett. 1984, 25, 4613.
9. Deshong, P.; Kell, D. A. Tetrahedron Lett. 1986, 27, 3979.
10. Takano, S.; Iwabuchi, Y.; Ogasawara, K. J. Am. Chem. Soc. 1987, 109, 5523
11. Takano, S.; Iwabuchi, Y.; Ogasawara, K. J. Chem. Soc., Chem. Commun. 1988, 1204.
12. Confalone, P. N.; Huie, E. M. J. Am. Chem. Soc. 1984, 106, 7175.
13. Coldham, L.; Coles, S. J.; Crapnell, K. M.; Fernandez, J.-C.; Haxell, T. F. N.; Hursthouse, M. B.; Moseley, J. D.; Treacy, A. B. Chem. Commun. 1999, 1757.
14. a) Lovely, C. J.; Mahmud, H. Tetrahedron Lett. 1999, 40, 2079.
15. b) Snider, B. B.; Ahn, Y.; Foxman, B. M. Tetrahedron Lett. 1999, 40, 3339.
16. Padwa, A.; Ku, H. J. Org. Chem. 1979, 44, 255.
17. DeShong, P.; Kell, D. A.; Sidler, D. R. J. Org. Chem. 1985, 50, 2309.
18. (a) Wenkert, D.; Ferguson, S. B.; Porter, B.; Qvarnstrom, A. J. Org. Chem. 1985, 50, 4114.
19. (b) Eberbach, W.; Fritz, H.; Heinze, I.; Von Laer, P.; Link, P. Tetrahedron Lett. 1986, 27, 4003.
20. (a) Grigg, R.; Duffy, L. M.; Dorrity, M. J.; Malone, J. F.; Rajviroongit, S.; Thornton-Pett, M. Tetrahedron 1990, 46, 2213 and the references cited therein.
21. (b) Kanemasa, S.; Doi, K.; Wade, E. Bull. Chem. Soc. Jpn. 1990, 63, 2866.
22. (c) Confalone, P.; Earl, R. A. Tetrahedron Lett. 1986, 27, 2695.
23. (d) Harwood, L. M.; Lilley, I. A. Synlett 1996, 1010.
24. (e) Grigg, R.; Savic, V.; Thornton-Pett, M. Tetrahedron 1997, 53, 10633.
25. (f) Roussi, G. Heterocycles 1990, 31, 1445.
26. (g) Martin, S. F.; Cheavens, T. H. Tetrahedron Lett. 1989, 30, 7017.
27. (h) Marx, M. A.; Grillot, Anne-Laure.; Lourer, C. T.; Beaver, K. A.; Bartlett, P. A. J. Am. Chem. Soc. 1997, 119, 6153.
28. (i) Nayyar, N. K.; Hutchison, D. R.; Martinelli, M. J. J. Org. Chem. 1997, 62, 982.
29. (j) Gong, Young-Dae.; Najdi, S.; Olmstead, M. M.; Kurth, M. J. J. Org. Chem. 1998, 63, 3081.
30. (k) Harling, J. D.; Orlek, B. S. Tetrahedron 1998, 54, 14905.
31. (a) Denhart, D. J.; Griffith, D. A.; Heathcock, C. H. J. Org. Chem. 1998, 63, 9616.
32. (b) Downham, R.; Ng, F. W.; Overman, L. E. J. Org. Chem. 1998, 63, 8096.
33. Armstrong, P.; Grigg, R.; Jordan, M. W.; Malone, J. F. Tetrahedron 1985, 41, 3547.
34. (a) Mehta, G.; Prabhakar, C. J. Org. Chem. 1995, 60, 4638.
35. (b) Tinant, B.; Feneau-Dupont, J.; Declercq, J-P.; De Boeck, B.; Viehe, H. G. J. Chem. Soc., Perkin Trans. 2 1992, 1821.
36. (c) Connolly, P. J.; Heathcock, C. H. J. Org. Chem. 1985, 50, 4135.
37. (d) Bell, M. R.; Oesterlin, R.; Geolotte, K. O.; Hlavac, A. G.; Crain, A. V. R., Jr. J. Heterocycl. Chem. 1977, 14, 1059.
38. Overmann, L. E.; Tellew, J. E. J. Org. Chem. 1996, 61, 8338.
39. Pandey, G.; Lakshmaiah, G.; Kumarswamy, G. J. Chem. Soc., Chem. Commun. 1992, 1313.
40. Pandey, G.; Lakshmaiah, G. Tetrahedron Lett. 1993, 34, 4861.
41. (a) Pandey, G.; Lakshmaiah, G. Synlett 1994, 277.
42. (b) Pandey, G.; Lakshmaiah, G.; Gadre, S. R. Ind. J. Chem. 1996, 35B, 91.
43. (a) Pandey, G.; Lakshmaiah, G.; Ghatak, A. Tetrahedron Lett. 1993, 34, 7301.
44. (b) Pandey, G.; Laha, J. K.; Mohanakrishnan, A. K. Tetrahedron Lett. 1999, 40, 6065.
45. (a) Pandey, G.; Bagul, T. D.; Lakshmaiah, G. Tetrahedron Lett. 1994, 35, 7439.
46. (b) Pandey, G.; Bagul, T. D.; Sahoo, A. K. J. Org. Chem. 1998, 63, 760.
47. Pandey, G.; Sahoo, A. K.; Gadre, S. R.; Bagul, T. D.; Phalgune, U. D. J. Org. Chem. 1999, 64, 4990.
48. Smith, M. P.; Johnson, K. M.; Zhang, M.; Flippen-Anderson, J. L.; Kozikowski, A. P. J. Am. Chem. Soc. 1998, 120, 9072.
49. Tamiz, A. P.; Smith, M. P.; Kozikowski, A. P. Bioorg. Med. Chem. Lett. 2000, 10, 297.
50. Pandey, G.; Sahoo, A. K.; Bagul, T. D. Org. Lett. 2000, 2, 2299.
51. Molander, G. A.; Harris, C. R. J. Org. Chem. 1997, 62, 7418.
52. (a) Pandey, G.; Hajra, S.; Ghorai, M. K.; Kumar, K. R. J. Am. Chem. Soc. 1997, 119, 8777.
53. (b) Pandey, G.; Hajra, S.; Ghorai, M. K.; Kumar, K. R. J. Org. Chem. 1997, 62, 5966.
54. Kermadec, D.; Prudhomme, M. Tetrahedron Lett. 1993, 34, 2757.
55. Kiddle, J. J.; Green, D. L. C.; Thompson, C. M. Tetrahedron 1995, 51, 2851.
56. Olah, G. A.; Narang, S. C.; Gupta, B. G. B.; Malhotra, R. J. Org. Chem. 1979, 44, 1247.
57. Mancuso, A. J.; Swern, D. Synthesis 1981, 165.
58. Chen, Z.; Trudell, M. Chem. Rev. 1996, 96, 1179.
59. Ramey, K. C.; Lini, D. C.; Moriarty, R. M.; Gopal, H.; Welsh, H. G. J. Am. Chem. Soc. 1967, 89, 2401.
60. Bunce, R. A.; Peeples, C. J.; Jones, P. B. J. Org. Chem. 1992, 57, 1727.