A. A. Ponomarev

Amino esters of heterocyclic dicarboxylic acids

The corresponding amino esters and their hydrochlorides and quaternary salts were obtained by the condensation of 2,5-furan- and 2,5-tetrahydrothiophenedicarboxylic acid chlorides with 1-methyl-, 1-ethyl-, or 1-butyl-3-hydroxypiperidines.

Investigation of 1-azabicyclic compounds

The conditions for carrying out the condensation of 1,2-dihydropyrrolizine, 2-methyl-1,2-dihydropyrrolizine, and 3-methyl-1,2-dihydropyrrolizine with ethylene oxide were investigated. The NMR spectra indicated that hydroxyethylation proceeds at the 5 and 7 positions of the 1,2-dihydropyrrolizine system.

Synthesis of ?-diketones of the furan and thiophene series

A method for obtaining β-diketones of the furan and thiophene series by acylation of cupric acetylacetonate with 5-nitro-2-furoyl, 2-thenoyl, and 5-nitro-2-thenoyl chlorides was developed.

Saturated nitrogen heterocyclic compounds

Results are given of research on the synthesis ofα-pyrrolidylalkan-3-ols by hydrogenating primary and secondary furan amines under pressure over Raney nickel in aqueous acid solution. Some views about the mechanism of the reaction are put forward. It is shown that the relative yields of theα-pyrrolidylalkan-3-ols and corresponding tetrahydrofuran amines depend both on structural peculiarities of the starting furan amine, and on the hydrogenation conditions.

Liquid phase hydrogenation of some heterocyclic nitrogen compounds over ruthenium catalysts

Results are given for the hydrogenation of some heterocyclic nitrogen compounds (pyrrole, pyridine, indole, quinoline, and acridine) and certain derivatives of them in the liquid phase under pressure, in the presence of ruthenium catalysts. The results obtained indicate that these catalysts are very effective, making it possible to obtain high yields of the corresponding saturated compounds. In the cases of quinoline and acridine, depending on the temperature, double bonds in the polycyclic systems can be selectively hydrogenated.

Saturated nitrogen ring compounds

Preparation of pyrrolidine derivatives by hydrogenating acid solutions of furan amines having the amino group at position 3, is extended to furfuryl -substituted cyclic amines. By this means are synthesized polycyclic systems hitherto undescribed in the literature, containing a pyrroldine ring with hydroxyalkyl and other substituents. Among these are derivatives of Cyclopentanopyrrolidine, Octahydroindole, etc.

Investigations in the field of 1-aza bicyclic compounds

As the result of a study of the condensation of acrylonitrile and 1,2-dihydropyrrolizines in the presence of AlCl3, 5-cyanoethyl-1,2-dihydropyrrolizines have been synthesized. Some of the properties of the compounds obtained have been studied and their IR spectra have been recorded.

Investigation of furan compounds L. Synthesis of N-alkyl- and N-aryl-substituted diureides of tetrahydrofuran-2,5- and tetrahydrothiophene-2,5-dicarboxylic acids

The corresponding diureides of tetrahydrofuran-2,5- and tetrahydrothiophene-2,5-dicarboxylic acids and the dithioureide of tetrahydrothiophene-2,5-dicarboxylic acid were obtained by the acylation of thiourea, urea, and its N-methyl-, N-tert-butyl- and N-phenyl derivatives with the acid dichlorides of tetrahydrofuran-2,5- and tetrahydrothiophene-2,5-dicarboxylic acids.

Saturated nitrogen-containing heterocycles: IV. Synthesis and properties of pyrrolidin-2-yl-and cycloalkanopyrrolidin-2-ylpropionic acids

A general method for the synthesis of pyrrolidinyland cycloalkanopyrrolidinylpropionic acids by the oxidation of the corresponding heterocyclic alcohols has been developed. Some of those compounds have been converted into the corresponding methyl esters and pyrrolizidin-3-ones. Preliminary pharmacological tests have shown that the pyrrolizidin-3-ones possess a sedative effect.

Synthesis of (1-methyl-3-piperidylidene)di(2-thienyl)methane citrate (bithiodine)

An improved method of synthesizing (1-methyl-3-piperidylidene)di-(2-thienyl) methane citrate, starting from ethyl pyridine-3-carboxyla:e (ethyl nicotinate).