Abstract:
Irradiation of (-)-quebrachamine, a C4N-C5N-C6-C8N four-ring system, gives a 16-hydroxy derivative of a C4N-C5N-C6-C6-C6N five-ring system (a 16-hydroxy derivative of an ibogamine-like ring system). Some aspects of the photohydroxy cyclization reaction are discussed. © 1989, American Chemical Society. All rights reserved.
Referencias:
- Erra-Balsells, R., Frasca, A.R., (1984) Tetrahedron Lett., 25, p. 5363. , (b) Erra-Balsells, R.; Frasca, A. R. An. Asoc. Quim. Argentina 1985, 73, 207. (c) Erra-Balsells, R.; Frasca, A. R. Aust. J. Chem. 1988, 41, 103. (d) Erra-Balsells, R.; Frasca, A. R. An. Asoc. Quim. Argentina 1988, 76, 285
- Erra-Balsells, R., Frasca, A.R., (1983) Tetrahedron, 39, p. 33. , (b) Erra-Balsells, R. Phytochemistry, in press. (c) Biondic, M. C.; ErraBalsells, R. Photochemical Reaction of β-Carbolines in Carbon Tetrachloride-Ethanol mixtures, unpublished work
- Singh, S.O., Stenberg, V.I., Parmar, S.S., (1980) Chem. Rev., 80, p. 269. , (b) Torrenegra, R.; Pedrozo, J. A.; Achenbach, H.; Bauereis, P. Phytochemistry 1988, 27, 1843
- Craveiro, A.A., Matos, F.J.A., Serur, L.M., (1983) Phytochemistry, 22, p. 1526
- Qureshi, A.A., Scott, A.J., (1968) J. Chem. Soc. Chem. Commun., 945, p. 947
- Ban, Y., Yoshida, K., Goto, J., Oishi, T., Takeda, E., (1983) Tetrahedron, 39, p. 3657
- Yoshida, K., Nomura, S., Ban, Y., (1985) Tetrahedron, 41, p. 5495
- Ban, Y., Yoshida, K., Goto, J., Oishi, T., (1981) J. Am. Chem. Soc., 103, p. 6990
- Yoshida, K., Nomura, S., Nishibata, Y., Ban, Y., (1986) Heterocycles, 24, p. 2239
- Hesse, M., Bernhard, H.O., Progess in Mass Spectrometry (1975), 3. , (b) Hesse, M. Progress in Mass Spectrometry, Indolalkaloide; Verlag Chemie: Weinheim, 1974; Vol. 1. Alkaoide; Verlag Chemie: Weinheim; Spiteller-Friedmann, M., Kaschnitz, R., Spiteller, G., Chatterjee, A., Aditvachaudhurv, N., Ganguli, G., (1964) Monatsh. Chem., 95, p. 1228
- Dugan, J.J., Hesse, M., Renner, U., Schmid, H., (1967) Helv. Chim. Acta, 50, p. 65
- Kalaus, G., Malkieh, N., Kajtar-Peredy, M., Brlik, J., Szabo, L., Szantav, C., (1988) J. Org. Chem., 53, p. 42
- Zaman, K., Atta-Ur-Rahman (1988) Phytochemistry, 27, p. 1926
- Wenkert, E., Cochran, D.W., Gottlieb, H.E., Hagaman, E.W., Braz Filho, R., de Abreu Matos, F.J., Madruga, M.I., (1976) Helv. Chim. Acta, 59, p. 2437. , (b) Wenkert, E.; Hagaman, E. W.; Kunesch. N.; Wang, N. Y. ; Zsadom. B. Phytochemistry 1976, 59, 2711
- Erra-Balsells, R.J., (1988) Heterocycl. Chem, 25, p. 1059. , (b) Erra-Balsells, R.; Frasca, A. R. Magn. Reson. Chem., in press. (c) ErraBalsells. R. Magn. Reson. Chem. 1988, 26, 1109
- Morales-Rios, M.S., eira, J., Joseph-Nathan, P., (1987) Magn. Reson. Chem., 25, p. 377
- Budzikiewicz, H., Djerassi, C., Williams, D.H., Interpretation of Mass Spectra of Organic Compounds (1967), Holden Day Inc.: New York; Eliel, E.L., Stereochemistry of Carbon Compounds (1962), McGraw-Hill: New York; Nakagawa, M., Ohvoshi, N., Hino, T., (1976) Heterocycles, 4, p. 1275
- Sundberg, R.J., The Chemistry of Indoles (1970), Academic New York; Turro, N., (1978) J. Modern Molecular Photochemistry, , Benjamin Menlo Park
- Mudry, C.A., Frasca, A.R., (1973) Tetrahedron, 29, p. 603
- Leete, E., (1961) J. Am. Chem. Soc., 83, p. 3645. , (b) Ying-Hsiueh Chen, F.; Leete, E. Tetrahedron Lett. 1963, 2013. (c) Wasserman, H. H.; Floyd, M. B. Tetrahedron 1963, 2009
- Coyle, J.D., (1971) J. Chem. Soc. (B), p. 2254
- O'Neal, H.E., Miller, R.G., Gunderson, E., (1974) J. Am. Chem. Soc., 96, p. 3351. , (b) Sciano, P. J. J. Chem. Soc. Chem. Comm. 1972, 390
- Laqua, K., Melhuish, W.H., Zander, M., (1988) Pure Appl. Chem., 60, p. 1449
- Erra-Balsells, R., (1987) J. Heterocycl. Chem., 24, p. 1117. , (b) Erra-Balsells, R. J. Heterocycl. Chem. 1988, 25, 221. (c) Erra-Balsells, R. Mass Spectral Fragmentation Patterns of 2,3-polyMethylene nitroindales, unpuhlished work
- Shizuka, H., Tanaka, I., (1968) Bull. Chem. Soc. Jpn., 41, p. 2343. , (b) Braslavsky, S. E.; Kuhn, H. J. Provisional List of Actinometers; IUPAC, 1987
- Kaschnitz, R., Spiteller, G., (1965) Monatsh. Chem, 96, p. 909. , (b) Schumann, D.; Bycroft, B. W.; Schmid, H. Experientia 1964, 20, 202. (c) Klyne, W.; Swan, R. J.; Bycroft, B. W.; Schumann, D.; Schmid, H. Helv. Chim. Acta 1965, 48, 443. (d) Klyne, W.; Swan, R. J.; Dastoor, N. J.; Gormann. A. A.: Schmid. H. Helv. Chim. Acta 1967. 50. 115
- Markey, S., Biemann, K., Witkop, B., (1967) Tetrahedron Lett., p. 157
Citas:
---------- APA ----------
Postigo, J.A. & Erra-Balsells, R.
(1989)
. Photochemical Reaction of (-)-Quebrachamine. Unusual Photoformation of an Ibogamine-like Ring System. Journal of Organic Chemistry, 54(13), 3174-3176.
http://dx.doi.org/10.1021/jo00274a038---------- CHICAGO ----------
Postigo, J.A., Erra-Balsells, R.
"Photochemical Reaction of (-)-Quebrachamine. Unusual Photoformation of an Ibogamine-like Ring System"
. Journal of Organic Chemistry 54, no. 13
(1989) : 3174-3176.
http://dx.doi.org/10.1021/jo00274a038---------- MLA ----------
Postigo, J.A., Erra-Balsells, R.
"Photochemical Reaction of (-)-Quebrachamine. Unusual Photoformation of an Ibogamine-like Ring System"
. Journal of Organic Chemistry, vol. 54, no. 13, 1989, pp. 3174-3176.
http://dx.doi.org/10.1021/jo00274a038---------- VANCOUVER ----------
Postigo, J.A., Erra-Balsells, R. Photochemical Reaction of (-)-Quebrachamine. Unusual Photoformation of an Ibogamine-like Ring System. J. Org. Chem. 1989;54(13):3174-3176.
http://dx.doi.org/10.1021/jo00274a038