A three-step synthesis of potentially biologically active 30- and 32-membered macroheterocycles with esters and acylhydrazines starting from methyl undecylenate was developed based on [1+1]-condensation of intermediate tetraesters, i.e., bis(10′ -methoxy-10′-oxodecyl)- or bis(11′-methoxy-11′ -oxoundecyl)hexanedioate, with hydrazine hydrate. The structures of the synthesized compounds were confirmed using IR and NMR spectroscopy and mass spectrometry.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
L. G. Chekanova, T. D. Batueva, A. V. Radushev, and A. V. Kataev, Russ. J. Inorg. Chem., 11, 1390 (2013).
A. N. Antimonova, N. I. Petrenko, M. M. Shakirov, M. A. Pokrovskii, A. G. Pokrovskii, and E. E. Shul’ts, Chem. Nat. Compd., 50, 1016 (2014).
E. E. Lakontseva and M. Yu. Krasavin, Izv. Vyssh. Uchebn. Zaved., Khim. Khim. Tekhnol., 5, 28 (2010).
G. Yu. Ishmuratov, M. P. Yakovleva, G. R. Mingaleeva, M. A. Shutova, R. R. Muslukhov, E. M. Viripaev, and A. G. Tolstikov, Macroheterocycles, 3, 246 (2012).
G. Yu. Ishmuratov, M. P. Yakovleva, G. R. Mingaleeva, M. A. Shutova, R. R. Muslukhov, E. M. Viripaev, and A. G. Tolstikov, Macroheterocycles, 2, 180 (2013).
D. J. Anneken, S. Both, R. Christoph, G. Fieg, U. Steinberner, and A. Westfechtel, “Fatty Acids,” in: Ullmann′s Encyclopedia of Industrial Chemistry, Vol. 14, Wiley-VCH, Weinheim, 2006, p. 73.
G. Yu. Ishmuratov, M. P. Yakovleva, and G. A. Tolstikov, Chem. Nat. Compd., 36, 105 (2000).
I. L. Klunyants, Chemical Encyclopedia [in Russian], Vol. 2, Sovetskaya Entsiklopediya, Moscow, 1990, 792 pp.
M. S. F. Lie Ken Jie and D. W. Y. Leung, Lipids, 1, 1 (1990).
F. Benton and A. Kiess, J. Org. Chem., 3, 470 (1960).
A. J. Gordon and R. A. Ford, The Chemist’s Companion, Wiley-Interscience, New York, 1972.
N. Ya. Grigor’eva, P. G. Tsiklauri, and A. V. Buevich, Russ. Chem. Bull., 6, 1079 (1994).
N. Yamamoto, Y. Obora, and Y. Ishii, J. Org. Chem., 8, 2937 (2011).
K. Weygand and G. Hilgetag, Organisch-chemische Experimentierkunst, Barth, Leipzig, 1964.
Acknowledgment
The work was financially supported by RAS program “Basic Principles of Chemistry” on topic No. 8 “Chemo-, regio-, and stereoselective transformations of terpenoids, steroids, and lipids for targeted synthesis of low-molecular-mass bioregulators” (State Reg. No. AAAA-A17-117011910023-2, 2017).
Author information
Authors and Affiliations
Corresponding author
Additional information
Translated from Khimiya Prirodnykh Soedinenii, No. 5, September–October, 2019, pp. 770–772.
Rights and permissions
About this article
Cite this article
Mingaleeva, G.R., Yakovleva, M.P. & Ishmuratov, G.Y. Synthesis from Undecylenic Acid of Macroheterocycles with Diacylhydrazine and Ester Fragments. Chem Nat Compd 55, 895–898 (2019). https://doi.org/10.1007/s10600-019-02840-2
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10600-019-02840-2