The alkylation reaction of aromatic acidshydrazides with (±)-cis-3-dichloromethyl-1,2,2-trimethylcyclopentancarboxylic acid

Ye. A. Tsapko


The article describes the study of the alkylation reaction of aromatic acids hydrazides with (±)-cis-3-dichloromethyl-1,2,2-trimethylcyclopentancarboxylic acid. The acid mentioned is a new substance obtained by oxidative cleavage of racemic camphor in the tetrachloromethane medium according to the method described earlier and modified by us. As a result of alkylation of aromatic acids hydrazides, a series of 3-{[2-(R-carbonyl)hydrazinylidene] methyl}-1,2,2-trimethylcyclopentancarboxylic acids has been obtained with the yields of 77-88%. According to the data of 1H NMR spectra almost all products are E-isomers. The reaction of alkylation of anthranilic hydrazide proceeds with formation of the 1,2,3,4-tetrahydroquinazolin-4-one cycle and obtaining of (±)-cis-3-(3-аmіnо-1,2,3,4-tetrahydroquinazolin-4-оn-2-yl)-1,2,2-trimethylcyclopentancarboxylic acid. The composition of the compounds synthesized has been proven by elemental analysis , and their structure has been confirmed by 1H NMR spectroscopy. According to the results of PASS prediction the compounds synthesized are otential diuretic, antiviral and antibacterial agents. The synthetic studies conducted show the possibility of using (±)-cis-3-dichloromethyl-1,2,2-trimethylcyclopentancarboxylic acid as a building block for extension of a number of biologically active substances synthesized in our previous studies on the basis of (±)-cis-1,2,2-trimethylcyclopentan-1,3-dicarboxylic (camphoric) acid.


(±)-cis-3-dichloromethyl-1,2,2-trimethylcyclopentancarboxylic acid; hydrazides; hydrazones; alkylation

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Tsapko Ye. O., Grytsenko I. S., Maloshtan L. M., Tymoshina I. O., Sytnik К. М., Yakovleva L. V., Shapoval O. M. Current issues of pharmaceutical and medical science and practice, 2013, Vol. 13, No.3, pp.106-108.

Tsapko Ye. O., Grytsenko I. S., Samura B. A., Nikolaev V. O. Medicines to human: modern problems of creation and testing of drugs: materials XXV jubilee scientific and practical conference, Kharkov, 2008, pp.388-393.

Tsapko Ye. O., Grytsenko I. S., Krasilnikova O. A., Bushlya N. E. Visnyk farmaciyi – Bulletin of pharmacy, 2007, No.3(51), pp.12-17.

Meyers C. Y., Kolb V. M. J. Org. Chem., 1978, Vol. 43, No.10, рр.1985-1990.

Pat. US 3896164. – Publ. 22.07.75.

Garcı́aa O., Nicolása E., Albericio F. Tetrahedron Lett., 1983, Vol. 44, No.27, pp.4961-4963, doi:10.1016/S0040-4039(03)01168-7.

Reutrakul V., Herunsalee K. Tetrahedron Lett. 1983, Vol. 24, No.5, pp.527-530, doi:10.1016/S0040-4039(00)81455-0.

Claridge T. D. W. High-resolution NMR Techniques in Organic Chemistry. Newnes, 2009, 383 p. 10. Seshaiah K. S., Muniyandy S., Atmakuru R. Eur. J. Med. Chem., 2001, Vol. 36, No.7-8, pp.615-625, doi:


Inam A., Siddiqui S. M., Macedo T. S., Moreira D. R. M., Leite A. C. L., Soares M. B. P., Azam A. Eur. J. Med. Chem., 2014, Vol.75, pp.67-76.

Backes G. L., Neumann D. M., Jursic B. S. Bioorg. Med. Chem., 2014, in Press, doi: 10.1016/j.bmc.2014.07.022.

Neumann D. M., Cammarata A., Backes G., Palmer G. E., Jursic B. S. Bioorg. Med. Chem., 2014, Vol. 22, No.2, pp.813-826, doi: 10.1016/j.bmc.2013.12.010.

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