E. B. Rakhimova

Multicomponent reactions of amines with aldehydes and H2S as efficient route to heterocycles and thioaza macrocycles

Here we provide new experimental results on multicomponent reactions of amines with aldehydes and H2S in the directed synthesis of functionally-substituted 1,3-thiazetidines, 1,3,5-dithiazinanes, 1,3,5-thiadiazinanes, 1,5-dithia-3,7-diazacyclooctanes, and thioaza macrocycles. X-ray analysis gave insight into the structure of the synthesized compounds. New kinds of multicomponent reactions (MCR) have been discovered and characterized.

Effective synthesis of N-aryl-substituted 1,5,3-dithiazepinanes and 1,5,3-dithiazocinanes

Selective methods were developed for the synthesis of N-aryl-1,5,3-dithiazepinanes and N-aryl-1,5,3-dithiazocinanes by transamination of N-tert-butyl-1,5,3-dithiazepinane or recyclization of 1-oxa-3,6-dithiacycloheptane and 1-oxa-3,7-dithiacyclooctane by the action of aniline derivatives in the presence of Sm(NO3)3·6H2O catalyst.

One-pot cyclothiomethylation of amines as efficient method for the synthesis of saturated five-, six-, seven-, and eight-membered S,N-Heterocycles

The review generalizes and systemizes published data on the synthesis of biologically active saturated five-, six-, seven-, and eight-membered S,N-heterocycles. Particular attention is given to cyclothiomethylation of various amines by the action of two-component systems CH2O-H2S (or thiols) and RCHO-CS2 (or S2Cl2).

Synthesis of α,ω-Bis-1,5,3-dithiazepanes and Their Fungicidal Properties

A procedure was developed for preparative synthesis of α,ω-bis-1,5,3-dithiazepanes by heterocyclization of aliphatic α,ω-diamines with N,N,N′,N′-tetramethylmethanediamine and 1,2-ethanedithiol. The fungicidal activity of 1,2-bis(1,5,3-dithiazepan-3-yl)ethane and 3,3′-(3,6-dioxaoctane-1,8-diyl)bis-1,5,3-dithiazepane toward microscopic fungi affecting agricultural plants was studied.

Efficient catalytic synthesis of (1,5,3-dithiazepan-3-yl)quinolines

Abstract(1,5,3-Dithiazepan-3-yl)quinolines were obtained in high yields by the reaction of 1-oxa-3,6-dithiacycloheptane with quinolinamines in the presence of a catalyst Sm(NO3)3·6H2O.

Synthesis of N-Hydroxyalkyl-1,5,3-Dithiazepanes Based on Amino Alcohols

Catalytic methods were developed for the synthesis of N-hydroxyalkyl-1,5,3-dithiazepanes by recyclization of 1-oxa-3,6-dithiacycloheptane with amino alcohols and by intermolecular cyclization of 1,2-ethanedithiol with methoxymethylamino alcohols.

Cyclothiomethylation of Aliphatic Polyamines with Formaldehyde and Hydrogen Sulfide

Cyclothiomethylation of the terminal amino groups in N-(2-aminoethyl)ethane-1,2-diamine, N,N′-bis(2-aminoethyl)ethane-1,2-diamine, and N,N′-bis(2-aminoethyl)ethane-1,1-diamine with formaldehyde and hydrogen sulfide gave the corresponding bis-1,3,5-dithiazinane derivatives. The reaction in aqueous butanol at 0°C was accompanied by intermolecular thiomethylation at the secondary amino groups with formation of previously unknown polyheterocyclic compounds containing nitrogen and sulfur atoms.

New methods for the synthesis of α,ω-bis-1,5,3-dithiazepanes on the basis of aliphatic α,ω-diamines

Efficient methods for the synthesis of α,ω-bis-1,5,3-dithiazepanes based on the heterocyclization of α,ω-diamines with N1,N1,N6,N6-tetramethyl-2,5-dithiahexane-1,6-diamine and on the intermolecular cyclization of 1,2-ethanedithiol with tetrakis(methoxymethyl)diamines catalyzed by SmCl3∙6H2O have been developed.

Cyclothiomethylation of heterochain α,ω-diamines with formaldehyde and H2S

Cyclothiomethylation was performed of heterochain (O, S-S, NH) α,ω-diamines with formaldehyde and H2S in aqueous medium at 20–60°C to obtain new α,ω-bis(1,3,5-dithiazinanes). The cyclocondensation of N-(3-aminopropyl)butane-1,4-diamine (spermidine), formaldehyde, and H2S proceeds efficiently in the medium of BuOH-H2O at 0°C and leads to the formation of previously unknown O,S-containing macroheterocycle, 1,7-dioxa-3,5,9,11-tetrathiacyclododecane. A fungicidal activity was found in 5,5′-(3,6-dioxaoctane-1,8-diyl)bis-1,3,5-dithiazinane with respect to microscopic fungi affecting agriculture.

Effective synthesis of N -substituted 1,3,5-dithiazinanes by reactions of N -methyl-1,3,5-dithiazinane and 1,3,5-trithiane with aromatic amines

A novel procedure has been developed for selective synthesis of N-aryl-1,3,5-dithiazinanes, 1,2,6,7-tetrahydro-3,5,1,7-benzodithiadiazonine, and 6,7-dihydro-1,3,5,7-benzotrithiazonine by reactions of aniline derivatives with N-methyl-1,3,5-dithiazinane or 1,3,5-trithiane in the presence of transition and rare earth metal salts and complexes.