Artículos de revistas
13c Nmr Spectral Analysis Of Some Isoquinoline Alkaloids
Registro en:
Phytochemistry. , v. 17, n. 9, p. 1655 - 1658, 1978.
319422
10.1016/S0031-9422(00)94662-4
2-s2.0-0001031850
Autor
Marsaioli A.J.
Ruveda E.A.
Reis F.d.A.M.
Institución
Resumen
The 13C NMR spectra of some isoquinoline and tetrahydroisoquinoline alkaloids and their corresponding N-methosalts and of the bisbenzylisoquinoline alkaloid isochondodendrine were recorded and the signals assigned. The substituent shielding effects and the 13C1H long range couplings were analysed and utilized in the spectral interpretation. © 1978. 17 9 1655 1658 Wenkert, Buckwalter, Burffit, Gasić, Gottlieb, Hagaman, Schell, Wovkulich, (1976) Topics in Carbon-13 NMR Spectroscopy, 2. , G.C. Levy, Wiley-Interscience, New York Hughes, Holland, Maclean, (1976) Can. J. Chem., 54, p. 2252 Takao, Iwasa, Kamigauchi, Sigiura, (1977) Chem. Pharm. Bull., 25, p. 1426 Ferreira, de, Barata, Rúveda, (1977) Phytochemistry, , in press Compound 3 has a papaverine-like activity which is under study. Meirelles, U. M. F., Reis, F. A. M., Simioni, L. R., Magalhães, A. F., unpublished resultsJohns, Willing, 13C N.M.R spectra of quinoline and methylquinolines. The magnitude of the vicinal (peri)3JCCCHcoupling constants (1976) Australian Journal of Chemistry, 29, p. 1617 Marshall, Miiller, Conn, Seiwell, Ihrig, (1974) Accounts Chem. Res., 7, p. 333 Levy, Nelson, (1972) Carbon-13 Nuclear Magnetic Resonance for Organic Chemists, , Wiley-Interscience, New York Clark, Ewing, Scrowston, NMR studies of sulphur heterocycles: III—13C spectra of benzo[b]thiophene and the methylbenzo[b]thiophenes (1976) Organic Magnetic Resonance, 8, p. 252 Wenkert, E., pers. commBreitmaier, Spohn, (1973) Tetrahedron, 29, p. 1145 Yoshikawa, Morishima, Kunitomo, Ju-ichi, Yoshida, (1975) Chem. Lett., 961, p. 13. , A 3J(C8-H1) = 5.0 Hz observed in a fully coupled spectrum of 13, indicative of a close to 45° dihedral relationship, gives further support to this explanation Castelão, Jr., Gottlieb, de, Mesquita, Gottlieb, Wenkert, (1977) Phytochemistry, 16, p. 735 The fine structure of C7|3 3J(C7-H5) = 7.4 Hz| of 17, which becomes a multiplet in 18 and again a doublet | 3J(C7-H5) = 8.0 Hz | in 19, confirms the previous assignment. Methylation of 17 produces a crowded system in which the o-methyl group of C7 resonates, as expected, at lower fieldGaleffi, Marini-Bettolo, Vecchi, (1975) Gazz. Chim. Ital., 105, p. 1207 Franca, Giesbrecht, Gottlieb, Magalhães, Magalhães, (1975) Phytochemistry, 14, p. 1671 Pschorr, Ueberführung des Papaverins in eine vom Phenanthren sich ableitende Isochinolinbase (1904) Berichte der deutschen chemischen Gesellschaft, 37, p. 1926