Abstract
1-Bromo-and 1-iodo-6,14-endo-ethenodihydrothebaine-hydroquinones were obtained. The Heck reactions of these halides with various olefins were studied.
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A. F. Casy and R. T. Parfitt, Opioid Analgesics. Chemistry and Receptors, Plenum Press, New York-London, 1986.
L. Maat, Novel Thebainlike Morphinan-dienes and Their Diels-Alder Adducts, in Drugs of Abuse: Chemistry, Pharmacology, Immunology and AIDS, Eds P. T. K. Phan and K. Rice, NIDA Research Monograph, 1990, 35.
H. Schmidhammer, Progr. Med. Chem., 1998, 35, 83.
K. W. Bentley and A. F. Thomas, J. Chem. Soc., 1956, 1863.
G. A. Tolstikov, E. E. Shults, T. Sh. Mukhametyanova, and L. V. Spirikhin, Zh. Org. Khim., 1991, 27, 273 [J. Org. Chem. USSR, 1991, 27 (Engl. Transl.)].
G. A. Tolstikov, T. G. Tolstikova, E. E. Shults, T. Sh. Mukhametyanova, V. G. Popov, V. A. Davydova, D. N. Lazareva, and F. S. Zarudii, Khim.-Farm. Zh., 1992, 11, 39 [Pharm. Chem. J., 1992, 11 (Engl. Transl.)].
K. W. Bentley, D. G. Hardy, and B. Meek, J. Am. Chem. Soc., 1967, 89, 3273.
H. Schmidhammer and A. Brossi, J. Org. Chem., 1983, 48, 1469.
M. Spetea, F. Schüllner, R. C. Moisa, I. P. Bersetei-Gurske, B. Schraml, C. Dörfler, M. D. Aceto, L. S. Harris, A. Coop, and H. Schmidhammer, J. Med. Chem., 2004, 47, 3243.
M. P. Wentland, Q. Lu, R. Lou, Y. Bu, B. I. Knapp, and J. M. Bidlack, Bioorg. Med. Chem. Lett., 2005, 15, 2107.
A. P. Terent’ev and L. A. Yanovskaya, Reaktsii i metody issledovaniya organicheskikh soedinenii [Reactions and Methods of Investigations of Organic Compounds], Goskhimizdat, Moscow, 1957, 6, 7 (in Russian).
M. A. Rodriguez-Franco, I. Dorronsoro, A. I. Hernandez-Higueras, and G. Antequera, Tetrahedron Lett., 2001, 42, 863.
J. B. Stothers, Carbon-13 NMR Spectroscopy, Academic Press, New York-London, 1972.
K. Görlitzer and R. Schumann, Pharmazie, 1992, 47, 893.
Y. Nan, W. Xu, K. Zaw, K. E. Hughes, L.-F. Huang, W. J. Dunn, III, L. Bauer, and H. N. Bhargava, J. Heterocycl. Chem., 1997, 34, 1995.
V. T. Bauman, E. E. Shults, M. M. Shakirov, and G. A. Tolstikov, Zh. Org. Khim., 2007, 43, 529 [Russ. J. Org. Chem., 2007, 43 (Engl. Transl.)].
S. G. Davies and D. Pyatt, Heterocycles, 1989, 28, 163.
S. G. Davies, C. J. Goodwin, D. Pyatt, and A. D. Smith, J. Chem. Soc., Perkin Trans. 1, 2001, 1413.
S.-M. Anderson and A. Hallberg, J. Org. Chem., 1987, 52, 3529.
S. Hagishita, M. Yamada, K. Shirahase, T. Okada, Y. Murakami, Y. Ito, T. Matsuura, M. Wada, T. Kato, M. Ueno, Y. Chikazawa, K. Yamada, T. Uno, I. Teshirogi, and M. Ohtani, J. Med. Chem., 1996, 39, 3636.
L. E. Rueter, D. J. Anderson, C. A. Briggs, D. L. Donnelly-Roberts, G. A. Gintant, M. Gopalakrishnan, N. H. Lin, M. A. Osinski, G. A. Reinhart, M. J. Buckley, R. E. L. Martin, J. S. McDermott, L. C. Preusser, T. R. Seifert, Z. Su, B. F. Cox, M. W. Decker, and J. P. Sulliovan, CNS Drug Rev., 2004, 10, 167.
G. B. Shul’pin, Organicheskie reaktsii, kataliziruemye kompleksami metallov [Organic Reactions Catalyzed by Metal Complexes], Nauka, Moscow, 1988, 275 (in Russian).
Organic Syntheses, Coll. Vol.2, Ed. A. Blatt, New York, 1947, 196.
C. Schopf, K. von Gottberg, and W. Petri, Justus Liebigs Annalen Chem., 1938, 536, 216.
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Dedicated to the memory of Academician N. N. Vorozhtsov on the 100th anniversary of his birth.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 6, pp. 1206–1214, June, 2007.
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Bauman, V.T., Shults, E.E., Shakirov, M.M. et al. Synthetic transformations of isoquinoline alkaloids. Synthesis of new dihydrothebaine-hydroquinone derivatives. Russ Chem Bull 56, 1252–1260 (2007). https://doi.org/10.1007/s11172-007-0190-1
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DOI: https://doi.org/10.1007/s11172-007-0190-1