A new and efficient approach to the synthesis of nicotine and anabasine analogues

Journal of Heterocyclic Chemistry

Volumn 46, Issue 6, 2009, Pages 1252-1258

  Huang, Kun ^a   Ortiz Marciales, Margarita ^a   De Jesús, Melvin ^a   Stepanenko, Viatcheslav ^a  

^a UNIVERSITY OF PUERTO RICO   (Puerto Rico)

Author keywords

[No Author keywords available]

Indexed keywords

1 (PYRIDIN 3 YL) 4 TRIISOPROPYLSILYLOXYBUTAN 1 OL; 1 (PYRIDIN 3 YL)BUTANE 1,4 DIOL; 3 (1 BENZYLPYRROLIDIN 2 YL)PYRIDINE; 3 (1 METHYLPYRROLIDIN 2 YL)PYRIDINE; 3 (1 PROPYLPYRROLIDIN 2 YL)PYRIDINE; 3 [1 (2 METHOXYETHYL)PYRROLIDIN 2 YL]PYRIDINE; 3 [1 (3 METHOXYPROPYL)PYRROLIDIN 2 YL]PYRIDINE; 3 [1 (PROP 2 YNYL)PYRROLIDIN 2 YL]PYRIDINE; 6 HYDROXY 1 (PYRIDIN 3 YL)HEXAN 1 ONE; 6 METHOXY 3 (1 BENZYLPIPERIDIN 2 YL)PYRIDINE; 6 METHOXY 3 (1 METHYLPIPERIDIN 2 YL)PYRIDINE; 6 METHOXY 3 [1 (2 METHOXYETHYL)PIPERIDIN 2 YL]PYRIDINE; ANABASINE DERIVATIVE; ESTER DERIVATIVE; ETHYLENE GLYCOL; KETONE DERIVATIVE; NICOTINE DERIVATIVE; PYRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ASYMMETRIC SYNTHESIS; CATALYST; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOSELECTIVITY; RACEMIZATION;

EID: 72249102372     PISSN: 0022152X     EISSN: None     Source Type: Journal    
DOI: 10.1002/jhet.233     Document Type: Article

References (26)

1. (a) Karlin, A. Nat. Rev. Neurosci. 2002, 3, 102;
2. (b) Lloyd, G. K.; Williams, M. J. Pharmacol. Exp. Ther. 2000, 292, 461;
3. (c) Tonder, J. E.; Olesen, P. H. Curr Med Chem 2001, 8, 651;
4. (d) Jensen, A. A.; Frolund, B.; Liljefors, T.; Krogsgaard-Larsen, P. J Med Chem 2005, 48, 4705;
5. (e) Mastropaolo, J.; Rosse, R. B.; Deutsch, S. I. Behav Brain Res 2004, 153, 419.
6. Holladay, M. K.; Dart, M. J.; Lynch, J. K. J Med Chem 1997, 40, 4169.
7. (a) Shepard, H. H. Chemistry and Action of Insecticides; McGraw-Hill: New York, NY, 1951;
8. (b) Gorrod, J. W.; Jacob, P., III. Analytical Determination of Nicotine and Related Compounds and their Metabolites; Elsevier: New York, NY, 1999; Chapter 1, pp 1-9.
9. (a) McDonald, I. A.; Vernier, J.-M.; Cosford, N.; Corey-Naeve, J. Curr Pharm Des 1996, 2, 357;
10. (b) Cosford, N. D. P.; Bleicher, L.; Dawson, H.; Whitten, J. P.; Adams, P.; Chavez-Noriega, L.; Correa, L. D.; Crona, J. H.; Mahaffy, L. S.; Menzaghi, F. M.; Rao, T. S.; Reid, R.; Sacaan, A. I.; Santori, E.; Stauderman, K.; Whelan, K.; Lloyd, G. K.; McDonald, I. A. J Med Chem 1996, 39, 3235.
11. Garvey, D. S.; Wasicak, J. T.; Elliot, R. L.; Lebold, S. A.; Hettinger, A.-M.; Carrera, G. M.; Lin, N.-H.; He, Y.; Holladay, M. W.; Anderson, D. J.; Cadman, E. D.; Raszkiewicz, J. L.; Sullivan, J. P.; Aneric, S. P. J Med Chem 1994, 37, 4455.
12. Abood, L. G.; Lerner-Marmarosh, N.; Wang, D.; Saraswati, M. Med Chem Res 1993, 2, 552.
13. Wang, D. X.; Booth, H.; Lerner-Marmarosh, N.; Osdene, T. S.; Abood, L. G. Drug Dev Res 1998, 45, 10.
14. Bhatti, B. S.; Strachan, J.-P.; Breining, S. R.; Miller, C. H.; Tahiri, P.; Crooks, P. A.; Deo, N.; Day, C. S.; Caldwell, W. S. J Org Chem 2008, 73, 3497.
15. For other alternative methods see: (a) Wagner, F. F.; Comins, D. L. Tetrahedron, 2007, 63, 8065;
16. Extensive review: (b) Chelucci, G. Tetrahedron: Asymmetry 2005, 16, 2353;
17. (c) Baxendale, I. R.; Brusotti, G.; Matsuoka, M.; Ley, S. V. J Chem Soc Perkin Trans 1 2002, 143;
18. (d) Felpin, F.-X.; Girard, S.; Vo-Thanh, G.; Robins, R. J.; Villiéras, J.; Lebreton, J. J Org Chem 2001, 66, 6305.
19. Ohkawa, S.; Terao, J. S.; Terashita, Z. I.; Shibouta, Y.; Nishikawat, K. J Med Chem 1991, 34, 267.
20. Aceto, M. D.; Martin, B. R.; Uwaydah, I. M.; May, E. L.; Harris, L. S.; Izazola-Conde, C.; Deway, W. L.; Bradshaw, T. J.; Vincek, W. C. J Med Chem 1979, 22, 174.
21. (a) Stepanenko, V.; De Jesús, M.; Correa, W.; Vázquez, C.; Guzmán, I.; De la Cruz, W.; Ortiz-Marciales, M.; Barnes, C. L. Tetrahedron Lett 2007, 48, 5799;
22. (b) Stepanenko, V.; De Jesús, M.; Correa, W.; Guzmán, I.; Vázquez, C.; Ortiz, L.; Ortiz-Marciales, M. Tetrahedron: Asymmetry 2007, 18, 2738;
23. (c) Huang, K.; Ortiz-Marciales, M.; Merced, F. G.; Meléndez, H. J.; Correa, W.; De Jesús, M. J Org Chem 2008, 73, 4017.
24. Carmella, S. G.; Kagan, S. S.; Hecht, S. S. Chem Res Toxicol 1992, 5, 76.
25. Damaj, M. I.; Glassco, W.; Dukat, M.; May, E. L.; Glennon, R. A.; Martin, B. R. Drug Dev Res 1996, 38, 177.
26. Murahashi, S.; Mitsui, H.; Shiota, T.; Tsuda, T.; Watanabe, S. J Org Chem 1990, 55, 1736.