Synthesis of Macrolides with Hydrazide Fragments from Tetrahydropyran and 2,6-Pyridinedicarboxylic Acid

Gumer Yu. Ishmuratov, Marina P. Yakovleva,^@ Mariya A. Shutova, Niyaz R. Yaubasarov, Rinat R. Muslukhov, Evgeny M. Viripaev, and Alexander G. Tolstikov

Dedicated to the Corresponding Member of Russian Academy of Sciences Oscar I. Koifman on the occasion of his 70th Anniversary

Institute of Organic Chemistry, Ufa Scientific Centre of RAS, 450054 Ufa, Russia

^@Corresponding author E-mail: insect@anrb.ru

DOI: 10.6060/mhc140374y
Macroheterocycles 2014 7(3) 321-324

The synthesis of two potentially useful 23- and 29-membered macrolides containing a pyridine ring and dihydrazide fragments was developed starting from tetrahydropyran. It was based on [1+1]-condensation of 7’-oxooctyl-7-oxooctanoate and bis(7-oxooctyl)hexanedioate with 2,6- pyridinedicarboxylic acid hydrazide. The structure of the macrocycles obtained was confirmed using by IR and NMR spectroscopy and mass spectrometry.

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1. Ishmuratov G.Yu., Mingaleeva G.R., Yakovleva M.P., Muslukhov R.R., Shakhanova O.O., Viripaev E.M., Tolstikov A.G. Russ. J. Org. Chem. 2011, 47, 1410-1415
http://dx.doi.org/10.1134/S1070428011090259

2. Ishmuratov G.Yu., Mingaleeva G.R., Yakovleva M.P., Shakhanova O.O., Muslukhov R.R., Tolstikov A.G. Russ. J. Org. Chem. 2011, 47, 1416-1425
http://dx.doi.org/10.1134/S1070428011090260

3. Ishmuratov G.Yu., Yakovleva M.P., Mingaleeva G.R., Muslukhov RR, Viripaev E.M., Galkin E.G., Tolstikov A.G. Macroheterocycles 2011, 4, 50-57.
http://dx.doi.org/10.6060/mhc2011.1.11

4. Ishmuratov G.Yu., Yakovleva M.P., Mingaleeva G.R., Shutova M.A., Muslukhov R.R., Viripaev E.M., Tolstikov A.G. Russ. Chem. Bull., Int. Ed. 2013, 62, 217-219

5. Ishmuratov G.Yu., Yakovleva M.P., Mingaleeva G.R., Shutova M.A., Muslukhov R.R., Vyrypaev E.M., Tolstikov A.G. Chem. Nat. Compds 2013, 49, 691-693.
http://dx.doi.org/10.1007/s10600-013-0708-8

6. Ishmuratov G.Yu., Ismagilova A.F., Mingaleeva G.R., Chudov I.V., Yakovleva M.P., Muslukhov R.R., Kashipov R.N., Tolstikov A.G. Butlerov Commun. 2009, 16, 21-25.

7. Jia B., Hu Z.-Q., Deng X.-T., Cheng C.-X., Shi Sh.-M. Acta Cryst. 2006, 62E, o4902-o4903.

8. Zhang G., Zhang H., Ye H., Zhang Q. J. Chem. Chem. Eng. 2011, 5, 1041-1045

9. Gao M.Zh., Reibenspies J.H., Wang B., Xu Z.L., Zingaro R.A. J. Heterocycl. Chem. 2004, 41, 899-904.
http://dx.doi.org/10.1002/jhet.5570410609

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Synthesis of Macrolides with Hydrazide Fragments from Tetrahydropyran and 2,6-Pyridinedicarboxylic Acid

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