Protonation of aminoindoles

Tetrahedron

Volumn 56, Issue 29, 2000, Pages 5177-5183

  Diana, Patrizia ^a   Barraja, Paola ^a   Lauria, Antonino ^a   Almerico, Anna Maria ^a   Dattolo, Gaetano ^a   Cirrincione, Girolamo ^a  

^a UNIVERSITY OF PALERMO   (Italy)

Author keywords

Amines; Indoles; Protonation; Tautomerism

Indexed keywords

INDOLE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; DRUG STRUCTURE; PARTIAL DRUG SYNTHESIS; PRIORITY JOURNAL; PROTON TRANSPORT; REACTION ANALYSIS; STRUCTURE ANALYSIS;

EID: 0034647766     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(00)00180-0     Document Type: Article

References (26)

1. Jones R.A. Pyrroles and their Benzo Derivatives: Reactivity. Bird C.W., Cheeseman G.W.H. Comprehensive Heterocyclic Chemistry. 1984;299 Pergamon, Oxford.
2. Cirrincione G., Almerico A.M., Aiello E., Dattolo G. Adv. Heterocycl. Chem. 48:1990;65-175.
3. Cirrincione G., Almerico A.M., Dattolo G., Aiello E., Diana P., Grimaudo S., Barraja P., Mingoia F., Gancitano R.A. Eur. J. Med. Chem. 29:1994;889-891.
4. (a) Falkson, C. I; Ibrahim, J., Kirkwood, J. M., Coates, A. S., Atkins, M. B., Blum, R. H. J. Clin. Oncol. 1998, 16, 1743-1751.
5. (b) Viviani, S., Bonadonna, G., Santoro, A., Bonfante, V., Zanini, M., Devizzi, L., Soncini, F., Valagussa, P. J. J. Clin. Oncol. 1996, 14, 1421-1430.
6. © Lucas, U. S., Huang, A. T. Development in Oncology in Clinic Management of Melanoma; Siegler, H. F., Ed., Martinus Nijhoff, the Hague: The Netherlands, 1982; Vol. 5, p. 382.
7. (a) Newlands, E. S., Stevens, M. F. G., Wedge, S. R., Wheelhouse, R. T., Brock, C. Cancer Treat. Rep. 1997, 23, 35-61.
8. (b) Bleehen, N. M., Newlands, E. S., Lee, S. M., Thatcher, N., Selby, P., Calvert A. H., Rustin, G. J. S., Brampton, M., Stevens, M. F. G. J. Clin. Oncol. 1995, 13, 910-913.
9. © O'Reilly, S. M., Newlands, E. S., Glaser, M. G., Brampton, M., Rice-Edwards, J. M., Illinworth, R. D., Richards, P. G., Kennard, C., Colquhoun, I. R., Lewis, P., Stevens, M. F. G. Eur. J. Cancer 1993, 29A, 940-942.
10. (d) Newlands, E. S., Blackledge, G. R. P., Slack, J. A., Rustin, G. J. S., Smith, D. B., Stuart, N. S. A., Quarterman, C. P., Hoffman, R., Stevens, M. F. G., Brampton, M. H., Gibson, A. C. Br. J. Cancer 1992, 65, 287-291.
11. Jones R.A. Pyrroles and their Benzo Derivatives: Reactivity. Bird C.W., Cheeseman G.W.H. Comprehensive Heterocyclic Chemistry. 1984;298 Pergamon, Oxford.
12. Cirrincione G., Almerico A.M., Diana P., Barraja P., Mingoia F., Grimaudo S., Dattolo G., Aiello E. J. Heterocycl. Chem. 33:1996;161-168.
13. Cirrincione G., Almerico A.M., Diana P., Grimaudo S., Barraja P., Dattolo G., Aiello E. Il Farmaco. 51:1996;275-277.
14. (a) Pschorr, R., Hoppe, G. Ber. Dtsch. Chem. Ges. 1910, 43, 2543-2552.
15. (b) Golubeva, G. A., Portnov, Yu. N., Kost, A. N. Khim. Geter. Soedin. 1973, 511-515.
16. © Grob, C. A., Weissbach, O. Helv. Chim. Acta 1961, 44, 1748-1753.
17. (d) Kebrle, J., Hoffmann, K. Helv. Chim. Acta 1956, 39, 116-131.
18. (a) Black, P. J., Heffernan, M. L. Aust. J. Chem. 1965, 18, 353-361.
19. (b) Reinecke, M. G., Johnson, Jr., H. W., Sebastian, J. F. J. Am. Chem. Soc. 1969, 91, 3817-3822.
20. © Lallemand, J. Y., Bernath, J. Bull. Soc. Chim. Fr. 1970, 4091-4099.
21. (d) Rosenberg, E., Williamson, K. L., Roberts, J. D. Org. Magn. Reson. 1976, 8, 117-119.
22. Cohen L.A., Daly J.W., Kny H., Witkop B. J. Am. Chem. Soc. 82:1960;2184-2187.
23. (a) Cirrincione, G., Dattolo, G., Almerico, A. M., Aiello, E., Jones, R. A., Hinz, W. Tetrahedron 1987, 43, 5225-5228.
24. (b) Bruix, M., de Mendoza, J., Claramunt, R. M., Elguero, J. Mag. Res. Chem. 1985, 23, 367-374.
25. (a) Unangst, P. C. J. Heterocycl. Chem. 1983, 20, 495-499.
26. (b) Schmitt, J., Perrin, C., Langlois, M., Suquet, M. Bull. Soc. Chim. Fr. 1969, 1227-1234.