A novel approach to conformationally restricted analogues of nicotine and anabasine by an intramolecular Hamaguchi-Ibata reaction

Tetrahedron Letters

Volumn 41, Issue 5, 2000, Pages 759-762

  Sarkar, Tarun K ^a   Basak, Sankar ^a   Ghosh, Sunil K ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY   (India)

Author keywords

1,9 phenanthroline; Azaisobenzofuran; Domino reaction; Intramolecular cycloaddition

Indexed keywords

8,10 DICHLORO 1,2,3,4,5,6 HEXAHYDRO 6 HYDROXY 1 METHYL 1,9 PHENANTHROLINE 6 CARBOXYLIC ACID; ANABASINE DERIVATIVE; BENZOFURAN DERIVATIVE; NICOTINIC AGENT; PHENANTHROLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; DRUG ACTIVITY; DRUG CONFORMATION; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 0034728158     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)02148-6     Document Type: Article

References (17)

1. Chavdarian, C. G.; Seeman, J. I.; Wooten, J. B. J. Org. Chem. 1983, 48, 492 and references cited therein.
2. Vernier, J.-M.; Holsenback, H.; Cosford, N. D. P.; Whitten, J. P.; Menzaghi, F.; Reid, R.; Rao, T. S.; Sacaan, A. I.; Lloyd, G. K.; Suto, C. M.; Chavez-Noriega, L. E.; Washburn, M. S.; Urrutia, A.; McDonald, I. A. Bioorg. Med. Chem. Lett. 1998, 8, 2173.
3. Sarkar, T. K.; Ghosh, S. K.; Nandy, S. K.; Chow, T. J. Tetrahedron Lett. 1999, 40, 397.
4. Peters, O.; Friedrichsen, W. Tetrahedron Lett. 1995, 36, 8581.
5. Compounds 8-11, 15-18 and 20 exist as mixtures of rotamers in solution.
6. 2: C, 52.49; H, 4.69; N, 8.16; found: C, 52.73; H, 4.62; N, 8.10.
7. Baum, J. S.; Shook, D. A.; Davies, H. M. L.; Smith, H. D. Synth. Commun. 1987, 17, 1709.
8. Padwa, A.; Kappe, C. O.; Cochran, J. E.; Snyder, J. P. J. Org. Chem. 1997, 62, 2786.
9. This possibility is under investigation.
10. 3): δ 7.34 and 7.28 (s, 1H), 5.91-5.78 and 5.71-5.60 (m, 1H), 5.12-4.90 (m, 2H), 3.80 (d, 1H, J=16.2 Hz), 3.72 and 3.71 (s, 3H), 3.56 (d, 1H, J=16.2 Hz), 3.70-3.43 and 3.17-2.96 (m, 2H), 3.11 and 2.87 (s, 3H), 2.20-1.66 (m, 4H).
11. 3): δ 6.69 and 6.64 (s, 1H), 5.93-5.77 and 5.76-5.60 (m, 1H), 5.11-4.90 (m, 2H), 3.95 and 3.94 (s, 3H), 3.77 (d, 1H, J=16.2 Hz), 3.70 and 3.68 (s, 3H), 3.51 (d, 1H, J=16.2 Hz), 3.72-3.42 and 3.17-3.01 (m, 2H), 3.09 and 2.88 (s, 3H), 2.35-1.65 (m, 4H).
12. 14.
13. Ho, T.-L. Tandem Organic Reactions; Wiley-Interscience: New York, 1992; Frontiers in Organic Synthesis, Chem. Rev. 1996, 96, 1; Tietze, L. F.; Beifuss, U. Angew. Chem., Int. Ed. Engl. 1993, 32, 131; Padwa, A. Chem. Commun. 1998, 1417.
14. Ho, T.-L. Tandem Organic Reactions; Wiley-Interscience: New York, 1992; Frontiers in Organic Synthesis, Chem. Rev. 1996, 96, 1; Tietze, L. F.; Beifuss, U. Angew. Chem., Int. Ed. Engl. 1993, 32, 131; Padwa, A. Chem. Commun. 1998, 1417.
15. Ho, T.-L. Tandem Organic Reactions; Wiley-Interscience: New York, 1992; Frontiers in Organic Synthesis, Chem. Rev. 1996, 96, 1; Tietze, L. F.; Beifuss, U. Angew. Chem., Int. Ed. Engl. 1993, 32, 131; Padwa, A. Chem. Commun. 1998, 1417.
16. Ho, T.-L. Tandem Organic Reactions; Wiley-Interscience: New York, 1992; Frontiers in Organic Synthesis, Chem. Rev. 1996, 96, 1; Tietze, L. F.; Beifuss, U. Angew. Chem., Int. Ed. Engl. 1993, 32, 131; Padwa, A. Chem. Commun. 1998, 1417.
17. Pelisson, M. M. M.; da Silva, G. V. J.; Clive, D. L. J.; Coltart, D. M.; Hof, F. A. J. Heterocyclic Chem. 1999, 36, 653.