Abstract
The photooxidation of tropan derivatives by ketones was studied; the targeting of the reaction to the N-CH3 group with the formation of N-alkylation products and bis-tropan derivatives was demonstrated. The presence of two diastereomers in salts of N-alkyl derivatives of tropan was detected by PMR spectroscopy. An alternative method of synthesis of difficult-to-obtain amino alcohols was proposed.
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References
S. G. Cohen and N. M. Stein, J. Am. Chem. Soc.,93, 6542 (1971).
S. G. Cohen, A. Parola, and G. H. Parsons, Chem. Rev.,73, 141 (1973).
G. Ciamcian and A. Silber, Ber.,48, 193 (1915).
G. O. Schehck, Dechema-Monographien, No. 24, 105 (1955).
G. Porter and P. Suppan, Pure Appl. Chem., No. 9, 499 (1964).
J. N. Pitts and J. S. Wan, Jr., The Chemistry of the carbonyl Group, S. Patal (ed.), New York-London (1966).
A. M. Belostotskii, L. M. Kostochka, and A. P. Skoldinov, Khim. Geterotsikl. Soedin., No. 12, 1657 (1982).
L. M. Kostochka and A. P. Skoldinov, Zh. Orhan. Khim.,17, 2459 (1981).
S. P. Singh, D. Kaufman, and V. S. Stenberg, J. Heterocycl. Chem.,16, 625 (1979).
J. Santamaria, R. Ouchabane, and S. Rigaudy, Tetrahedron Lett.,30, 2927 (1989).
G. L. Closs, J. Am. Chem. Soc.,81, 5456 (1959).
R. Glasser, Qin-Ji Peng, and A. S. Perlin, J. Org. Chem.,53, 2172 (1988).
A. Landenburg, Ann. Chem.,217, 118 (1883).
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Scientific-Research Institute of Pharmacology, Russian Academy of Medical Sciences, Moscow 125315. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 179–183, February, 1995. Original article submitted September 5, 1994.
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Kostochka, L.M., Skoldinov, A.P. & Lezina, V.P. Photoinduced N-β-hydroxyalkylation of tropan derivatives. Chem Heterocycl Compd 31, 153–156 (1995). https://doi.org/10.1007/BF01169671
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DOI: https://doi.org/10.1007/BF01169671