P. V. Reshetov

Synthesis and stereochemistry of perhydroacridines (review)

Methods for the synthesis of isomeric perhydroacridines are reviewed. Their configurational and conformational features are discussed.

Carbonyl-containing spiro-dihydrofurans in reactions with ammonium acetate and hydrazine hydrate

It has been shown that 2-spiro(3-R-6,6-dimethyl-4-oxo-2,3,4,5,6,7-hexahydrobenzofuran)-2′-(5′, 5′-dimethylcyclohexane-1′,3′-diones) undergo conversions in reactions with ammonium acetate and hydrazine hydrate into substituted dihydropyridin-2-ones and tetrahydro-1,2-diazepin-7-ones respectively as a result of ring-opening of the spirodimedonyl fragment through the corresponding amides and hydrazides of δ-keto acids.

Saturated Nitrogen-containing Heterocycles. 20. Catalytic Reduction of N-Hydroxyethylpyridinium and Quinolinium Salts

Previously unknown N-(2-hydroxyethyl)perhydroquinolines and N-(2-hydroxyethyl)piperidines were synthesized by catalytic reduction of N-(2-hydroxyethyl)tetrahydroquinolinium and N-(2-hydroxyethyl)tetrahydropyridinium tetrafluoroborates. A scheme for the formation of the hydrogenation products is presented.

Synthesis and Anticholinesterase Activity of N-Oxyalkyl-substituted Pyridinium and Hydroquinolinium Salts and Their Isologs

N-oxyalkylpiperidines (perhydroquinolines), N-oxyalkylpyridinium (hydroquinolinium) salts, and oxazolo(oxazino)hydroquinolines obtained from 1,5-diketones and the products of their O-heterocyclization exhibit moderate anticholinesterase activity in comparison to that of galanthamine. The maximum inhibiting effect was observed for N-oxyalkylpyridinium salts.

Hydroamination of pyrylium salts

The catalytic reductive amination of pyrylium salts proceeded stereoselectively to give piperidine bases with a cis-structure. The reaction involved the formation of a pyridine intermediate; the course of the reaction depended on the structure of both the substrate and the aminating agent.

Azaheterocycles based on 1,5-diketones, cyclic β-ketols, and ethanolamine

The peculiarities of the hydroxyethylamination of 1,5-diketones and three-ring β-ketols under heterogeneous-catalysis conditions as a function of the type of carbonyl compound were ascertained. Catalytic hydroxyethylamination is a convenient preparative method for the production of N-β-hydroxyethyl derivatives of 2,3,5,6-dicycloalkanopiperidines and 9-substituted perhydroacridines.

Saturated nitrogencontaining heterocycles. 19. Catalytic reduction of 10- and 9,10-substitutedsym-octahydroacridinium salts

Abstract10-Methyl(phenyl)- and 9,10-diphenylperhydroacridines have been obtained by the catalytic reduction of 10- and 9,10-substituted sym-octahydroacridinium salts. Selective reduction of the furan ring occurred in the case of 9-(2-furyl)-10-phenyl-sym-octahydroacridinium perchlorate. The stereoisomeric composition of the reaction products has been established and a probable scheme for their formation has been proposed.

CATALYTIC HYDROGENATION OF PYRYLIUM SALTS

On catalytic reduction of 2,6-diphenylpyrylium salts, hydrogenolysis occurs at the C−O bond with the formation of 1,5-diphenylpentanes. The principal direction of the hydrogenation of 9-phenyl-sym-octahydroxanthylium tetrafluoroborate is the formation of a mixture of products of partial and complete reduction of the heterocycle. The structure of the substances obtained was established by IR and13C NMR spectroscopy.