Potentially useful 17-, and 22÷25-membered macrolides containing azine or hydrazide groups were synthesized from tetrahydropyran via [1+1]-condensation at room temperature of 7-oxooctyl-7-oxooctanoate, which was obtained via Tishchenko reaction from 7-oxooctanal, with hydrazine hydrate and hydrazides of several dicarboxylic acids.
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References
A. V. Bogatskii, Meso-macroheterocycles (Selected Works) [in Russian], Naukova Dumka, Kiev, 1986.
I. Yu. Strobykina, B. F. Garifullin, G. I. Kovylyaeva, V. E. Kataev, and R. Z. Musin, Zh. Obshch. Khim., 77, 1277 (2007).
V. N. Odinokov, G. Yu. Ishmuratov, and R. R. Vakhidov, Khim. Prir. Soedin., 524 (1995).
V. N. Odinokov, G. Yu. Ishmuratov, L. P. Botsman, R. R. Vakhidov, I. M. Ladenkova, T. A. Kargapol′tseva, and G. A. Tolstikov, Khim. Prir. Soedin., 423 (1992).
G. Yu. Ishmuratov, M. P. Yakovleva, K. A. Tambovtsev, Yu. V. Legostaeva, L. V. Kravchenko, N. M. Ishmuratova, and G. A. Tolstikov, Khim. Prir. Soedin., 58 (2008).
K. V. Vatsuro and G. L. Mishchenko, Name Reactions in Organic Chemistry [in Russian], Khimiya, Moscow, 1976.
E. Breitmaier and W. Voelter, 13 C NMR-Spectroscopy, Verlag Chemie GmbH, Weinheim, 1974.
E. Pretsch, Tables of Spectral Data for Structure Determination of Organic Compounds, Springer-Verlag, Berlin, New York, 1983.
E. Pretsch, Tabellen zur Strukturaufklarung organischer Verbindungen mit spectroskopischen Methoden, Springer-Verlag, Berlin, New York, 1976.
D. Barton and W. D. Ollis, Comprehensive Organic Chemistry: The Synthesis and Reactions of Organic Compounds, Pergamon Press, Oxford, New York, 1979.
V. V. Takhistov and D. A. Ponomarov, Organic Mass Spectrometry [in Russian], VVM, St. Petersburg, 2005.
R. B. Sharma, A. T. Blades, and P. Kebarle, J. Am. Chem. Soc., 106, 510 (1984).
G. Yu. Ishmuratov, M. P. Yakovleva, L. P. Botsman, N. M. Ishmuratova, R. R. Muslukhov, G. V. Khambalova, and G. A. Tolstikov, Khim. Prir. Soedin., 28 (2003).
K. Weygand and G. Hilgetag, Organisch-chemische Experimentierkunst, Barth, Leipzig, 1964.
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Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 395–399, July–August, 2009.
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Ishmuratov, G.Y., Yakovleva, M.P., Mingaleeva, G.R. et al. Synthesis of macrolides with N-containing (azine or hydrazide) groups. Chem Nat Compd 45, 465 (2009). https://doi.org/10.1007/s10600-009-9406-y
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DOI: https://doi.org/10.1007/s10600-009-9406-y