Synthesis of semi-rigid analogs of anabasine

Tetrahedron Letters

Volumn 37, Issue 49, 1996, Pages 8841-8844

  Szczepanski, Steven W ^a   Anouna, Katherine G ^a  

^a FMC CORPORATION   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 AZABICYCLO[2.2.2]OCTANE DERIVATIVE; ANABASINE;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS;

EID: 0030566863     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02058-8     Document Type: Article

References (19)

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2. 2. See, a) Sattelle, D.B., Lummis, S.C.R., in Membrane Receptors and Enzymes as Targets of Insecticidal Action; Clark, J.M., Matsumura, F., Eds.; Plenum Press, New York, 1986, pp. 51-74.
3. b). Harrow, I.D., David, J.A., Sattelle, D.B. in Neuropharmacology of Insects Everd, D., O'Connor, M., Whelan, J., Eds.; Pitman Books, Lts. London, 1982, pp. 12-31
4. 3. For a review of the recent advances in nAChr therapeutics, see: McDonald, I.A., Cosford, N., Vermier, J-M. In Annual Reports in Medicinal Chemistry Vol. 30, Bristol, J.A., Ed.; Academic Press, SanDiego, CA, 1995, pp. 41-50.
5. 4. a) Spivak, C.E., Wiktop, B., Albuquerque, E.X. Mol. Pharmacol. 1980,18, 384-394.
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7. 5. a) Badio, B., Daly, J.W. Mol. Pharmacol. 1994, 45, 563-569;
8. b) Dukat, M., Damaj, M.I., Glassco, W., Dumas, D., May, E.L., Martin, B.R., Glennon, R.A. Med. Chem. Res. 1993, 4, 131-139.
9. 6. After the completion of this work, a patent was issued citing compounds 1 and 2 without experimental details. Piotrowski, D. W. PCT Int. Appl. WO 95 03 306, 1995.
10. 7. a) Merten, R., Muller, G. Angew. Chem. 1962, 74, 866.
11. b) Merten, R., Muller, G. Chem. Ber. 1964, 97, 6827.
12. 8 a) Cava, M.P., Wilkens, C.K., Jr. Chem. Ind. (London), 1964, 1422.
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14. 9. Quan, P.M., Karns, T.K.B., Quin, L.D. J. Org. Chem. 1965, 30, 2769-2772.
15. 13C NMR, IR, high resolution mass spectrometry and/or combustion analysis.
16. 2Cl 278.0822, found 278.0812. Characteristic resonances for the endo-isomer of 8b are δ6.00 (m, 1H), 4.70 and 4.78 (two s, 1H), 2.85 (br s, 1H).
17. 12. Krow, G.R., Rodebaugh, R., Carmosin, R., Figures, W., Pannella, H., DeVicaris, G., Grippi, M. J. Amer. Chem. Soc. 1973, 95, 5273-5280.
18. 3) δ8.51 (m, 2H), 7.56 (appt. dt, 1H, J = 2.1, 7.5 Hz), 7.25 (m, 1H), 4.86 and 4.79 (two br s, 1H), 4.33 and 4.18 (two s, 1H), 3.71 and 3.52 (two brs, 3H), 2.10-1.80 (br m, 5H), 1.66 (m, 2H), 1.33 (m, 2H).
19. 3, 300 MHz) δ 8.66 (d, 1H, J = 2.1 Hz), 8.46 (dd, 1H, J = 1.5, 4.6 Hz), 7.91 (dt, 1H, J = 8, 2 Hz), 7.27 (m, 1H), 4.36 (m, 1H), 4.36 (m, 1H), 3.49 (s, 1H), 3.07 (m, 1H), 2.14-1.69 (m, 6H), 1.53 (m, 2H), 1.32 (m, 1H).