Diastereoselective synthesis of nicotine derivatives via 1,3-dipolar cycloaddition reactions

Journal of Heterocyclic Chemistry

Volumn 47, Issue 3, 2010, Pages 611-615

  Ghandi, Mehdi ^a   Taheri, Abuzar ^a   Abbasi, Alireza ^a  

^a UNIVERSITY OF TEHRAN   (Iran)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLCHOLINE; ALDEHYDE; AZOMETHINE YLIDE; MALONONITRILE; N METHYL 4 (3 METHOXYPHENYL) 2 (PYRIDINE 3 YL)PYRROLIDINE 3,3 DICARBONITRILE; N METHYL 4 (3,4 METHOXYPHENYL) 2 (PYRIDINE 3 YL)PYRROLIDINE 3,3 DICARBONITRILE; N METHYL 4 (3,4,5 METHOXYPHENYL) 2 (PYRIDINE 3 YL)PYRROLIDINE 3,3 DICARBONITRILE; N METHYL 4 (4 BROMOPHENYL) 2 (PYRIDINE 3 YL)PYRROLIDINE 3,3 DICARBONITRILE; N METHYL 4 (4 CHLOROPHENYL) 2 (PYRIDINE 3 YL)PYRROLIDINE 3,3 DICARBONITRILE; N METHYL 4 (4 METHOXYPHENYL) 2 (PYRIDINE 3 YL)PYRROLIDINE 3,3 DICARBONITRILE; N METHYL 4 (4 METHYLPHENYL) 2 (PYRIDINE 3 YL)PYRROLIDINE 3,3 DICARBONITRILE; N METHYL 4 (4 NITROPHENYL) 2 (PYRIDINE 3 YL)PYRROLIDINE 3,3 DICARBONITRILE; N METHYL 4 BIPHENYL 2 (PYRIDINE 3 YL) PYRROLIDINE 3,3 DICARBONITRILE; N METHYL 4 PHENYL 2 (PYRIDINE 3 YL)PYRROLIDINE 3,3 DICARBONITRILE; NICOTINE DERIVATIVE; PYRIDINE DERIVATIVE; SARCOSINE; SPIRO[9,4] 1 N METHYL 2(PYRIDINE 3 YL)PYRROLIDINE 3,3 DICARBONITRILE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CYCLOADDITION; DIASTEREOISOMER; DRUG PROTEIN BINDING; DRUG SYNTHESIS; MASS SPECTROMETRY; ONE POT SYNTHESIS; PROTON NUCLEAR MAGNETIC RESONANCE; X RAY CRYSTALLOGRAPHY;

EID: 77953015711     PISSN: 0022152X     EISSN: 19435193     Source Type: Journal    
DOI: 10.1002/jhet.366     Document Type: Article

References (21)

1. (a) Pailer, M. In Tobacco Alkaloids and Related Compounds; von Euler, U. S., Ed.; Pergamon: New York, 1965; p 15;
2. (b) Gorrod, J. W.; Jacob, P. In Analytical Determination of Nicotine and Related Compounds and Their Metabolites; Elsevier: New York, 1999; pp 1-9.
3. Shepard, H. H. In The Chemistry and Action of Insecticides; McGraw-Hill: New York, 1951.
4. (a) Levin, E. D. J Neurobiol 2002, 53, 633;
5. (b) Newhouse, P. A.; Kelton, M. Pharm Acta Helv 2000, 74, 91;
6. (c) Holladay, M. K.; Dart, M. J.; Lynch, J. K. J Med Chem 1997, 40, 4169;
7. (d) Breining, S. R. Curr Top Med Chem 2004, 4, 609;
8. (e) Jensen, A. A.; Frølund, B.; Liljefors, T.; Krosgsgaard-Larsen, P. J Med Chem 2005, 48, 4705.
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.; Bleiker, 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. Ondachi, P. W.; Comins, D. L. Tetrahedron Lett 2008, 49, 569.
12. Smith, E. D.; Février, F. C.; Comins, D. L. Org Lett 2006, 8, 179.
13. (a) Gurpinder, S.; Ishar, M. P. S.; Girdhar, N. K.; Singh, L. J Heterocycl Chem 2005, 42, 1047;
14. (b) Gurpinder, S.; Munusamy, E.; Venkatesan, S.; Ishar, M. P. S. Heterocycles 2006, 68, 1409.
15. (a) Ramesh, E.; Kathiresan, M.; Raghunathan, R. Tetrahedron Lett 2007, 48, 1835;
16. (b) Wang, C.; Liang, G.; Xue, Z.; Gao, F. J Am Chem Soc 2008, 130, 17250;
17. (c) Ghandi, M.; Tabatabaei Rezaei, S. J.; Yari, A.; Taheri, A. Tetrahedron Lett 2008, 49, 5899;
18. (d) Ghandi, M.; Yari, A.; Tabatabaei Rezaei, S. J.; Taheri, A. Tetrahedron Lett 2009, 50, 4724.
19. Pearson, W. H. In Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products; Padwa, A., Ed.; Wiley: New York, 2002; pp 170-172.
20. Zhai, H.; Liu, P.; Luo, S.; Fang, F.; Zhao, M. Org Lett 2002, 4, 4385.
21. Crystallographic data for 3a have been deposited at the Cambridge Crystallographic Data Centre with the deposition number CCDC 748115. Copies of these data can be obtained free of charge via www.ccdc.ca-m.ac.uk/conts/ retrieving.html (or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge, CB2 1EZ, UK; Fax: +44 1223 336 033; or e-mail: deposit@ccdc.cam.ac.uk).