Дослідження реакції алкілування гідразидів ароматичних кислот (±)-цис-3-дихлорометил-1,2,2-триметилциклопентанкарбоновою кислотою

• Дата: 2015
• Автор: Tsapko, Ye. A.
• Формат: Стаття
• Мова: English
• Опубліковано: National University of Pharmacy 2015
• Теми: (±)-cis-3-dichloromethyl-1; 2; 2-trimethylcyclopentancarboxylic acid; hydrazides; hydrazones; alkylation; UDC 547.599.6; 543; 632.514.6; 547.288.3; (±)-цис-3-дихлорметил-1; 2-триметилциклопентанкарбоновая кислота; гидразиды; гидразоны; алкилирование; УДК 547.599.6; (±)-цис-3-дихлорометил-1; 2-триметилциклопентанкарбонова кислота; гідразиди; гідразони; алкілування
• Онлайн доступ: https://ophcj.nuph.edu.ua/article/view/ophcj.15.844
• Назва журналу: Journal of Organic and Pharmaceutical Chemistry

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.