Abstract
The reaction of 2,3-dioxopyrrolo[2,1-a]isoquinolines with sodium borohydride, depending on the conditions under which it is carried out, can proceed by the route of hydrogenation or by the opening of the pyrrole ring. In the latter case, ketoesters, for which examples of reactions at the dicarbonyl and enamine fragments are presented, are formed.
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References
V. S. Shklyaev, B. B. Aleksandrov, A. G. Mikhailovskii, and M. I. Vakhrin, Khim. Geterotsikl. Soedin., No. 7, 963 (1987).
A. G. Mikhailovskii, V. S. Shklyaev, and B. B. Aleksandrov, Khim. Geterotsikl. Soedin., No. 6, 808 (1990).
A. G. Mikhailovskii and V. S. Shklyaev, Khim. Geterotsikl. Soedin., No. 7, 946 (1994).
A. G. Mikhailovskii and V. S. Shklyaev, Khim. Geterotsikl. Soedin., No. 5, 650 (1995).
A. G. Mikhailovskii, V. S. Shklyaev, A. V. Ignatenko, and M. I. Vakhrin, Khim. Geterotsikl. Soedin., No. 7, 934 (1995)
T. Sano and Y. Tsuda, J. Synth. Org. Chem. Jpn., 46, 49 (1988).
V. S. Shklyaev, B. B. Aleksandrov, G. I. Legotkina, M. I. Vakhrin, M. S. Gavrilov, and A. G. Mikhailovskii, Khim Geterotsikl. Soedin., No. 11, 1560 (1983).
M. D. Mashkovskii, Medicinal Agents [in Russian], Vol. 1, Meditsina, Moscow (1993), p. 516.
A. G. Mikhailovskii and V. S. Shkiyaev, Khim. Geterotsikl. Soedin., No. 12, 1697 (1995).
R. Huisger and H. Seidi, Tetrahedron Lett., No. 29, 2019 (1963).
B. B. Aleksandrov, M. S. Gavrilov, M. I. Vakhrin, and V. S. Shklyaev, Khim. Geterotsiki. Soedin., No. 6, 794 (1985).
M. Yu. Dormidontov, B. Ya. Syropyatov, R. Z. Dautova, B. B. Aleksandrov, V. S. Shklyaev, M. I. Vakhrin, and A. G. Mikhailovskii, Khim.-farm. Zh., No. 1, 22 (1990).
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Institute of Technical Chemistry, Urals Section (UrO), Russian Academy of Sciences (RAN), Perm' 614600. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 685–692, May, 1996. Original article submitted February 10, 1996.
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Mikhailovskii, A.G. Reactions of 2,3-dioxopyrrolo[2,1-a]isoquinolines with sodium borohydride and the properties of its products. Chem Heterocycl Compd 32, 590–595 (1996). https://doi.org/10.1007/BF01164792
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DOI: https://doi.org/10.1007/BF01164792