G. V. Pokhvisneva

Synthesis of methylene-bis(1-oxy-3,3-dialkyl-1-triazene 2-oxides) and their analogs

Synthetic procedures towards methylene-bis(1-oxy-3,3-dialkyl-1-triazene 2-oxides), the first representatives of a new class of promising exogenous nitric oxide (NO) donors, which can release NO in living organisms, were developed. Synthesis involves the reactions of salts of 1-hydroxy-3,3-dialkyl-1-triazene 2-oxides with either dibromomethane or 1-chloromethoxy-3,3-dialkyl-1-triazene 2-oxides.

Synthesis and properties of 2-hydroxyethyl derivatives of methylene-bis(1-oxy-3, 3-dialkyl-1-triazene 2-oxides)

Synthetic approach to 2-hydroxyethyl derivatives of methylene-bis(1-oxy-3, 3-dialkyl-1triazene 2-oxides), promising NO donors, which can release NO in living organisms was developed. Some transformations of the hydroxyethyl moiety of the synthesized compounds were studied.

3-Amino-4-(α-nitroalkyl- ONN -azoxy)furazans and some of their derivatives

Synthetic procedures towards 3-amino-4-(a-nitroalkyl-ONN-azoxy)furazans and their derivatives involving nucleophilic displacement of the nitro group of 3-nitro-4-(a-nitroalkyl-ONN-azoxy)furazans on treatment with ammonia, primary and secondary amines, including diamines, were developed.

Synthesis of 1-alkoxy-3-methyl-1-triazene 2-oxides and 3, 3´-methylene-bis(1-alkoxy-3-methyl-1-triazene 2-oxides)

A method for the synthesis of 1-alkoxy-3-methyl-1-triazene 2-oxides and their salts with alkali metals was developed. 3, 3´-Methylene-bis(1-alkoxy-3-methyl-1-triazene 2-oxides) were obtained for the first time. Some properties of the synthesized compounds were studied. These compounds can be of interest as new NO and HNO donors in living organisms.

Bis(nitro- and polynitromethyl-ONN-azoxy)azoxyfurazans and some of their derivatives

Reaction of diamino derivative of azoxyfurazan with 2,2-dimethyl-5-nitro-5-nitroso-1,3-dioxane in the presence of dibromoisocyanuric acid afforded bis(2,2-dimethyl-5-nitro-1,3-dioxan-5-yl-ONN-azoxy)azoxyfurazan. The reaction of the latter with AcCl/MeOH and further transformations of the product gave the first representative of substituted (mono- and polynitroalkyl-ONN-azoxy)azoxyfurazans, e.g. bis(nitromethyl-ONN-azoxy)azoxyfurazan, bis(dinitromethyl-ONN-azoxy)azoxyfurazan, bis(trinitromethyl-ONN-azoxy)azoxyfurazan, and some of their derivatives.

Alkylation of 1-alkoxy-3-methyl-1-triazene 2-oxide sodium salts

Abstract1-Alkoxy-3-methyl-1-triazene 2-oxide sodium salts react with chloromethyl methyl sulfide to give a mixture of 1-alkoxy-3-methyl-3-(methylthiomethyl)-1-triazene 2-oxides and 3-alkoxy-1-methyl-3-(methylthiomethyl)-1-triazene 2-oxides. The reaction of these triazene oxide sodium salts with 3,3-dialkyl-1-chloromethoxy-1-triazene 2-oxides produces a complex mixture of product bearing the oxytriazene moieties of the starting alkoxy-1-triazene 2-oxides bonded with the methylene group as a key structural fragment.

Synthesis of 1,1’-[methylenebis(oxy)]-bis[3-alkyl-3-(2-hydroxyethyl)triaz-1-ene 2-oxides]

Potential NO donors, 1,1’-[methylenebis(oxy)]bis[3-(2-hydroxyethyl)triaz-1-ene 2-oxides], were derived from 3-alkyl-3-(2-acetoxyethyl)-1-chloromethoxytriaz-1-ene 2-oxides and 3-alkyl-1-hydroxy-3-(2-hydroxyethyl)triaz-1-ene 2-oxide sodium salts.

Synthesis of 3,3-bis(2-hydroxyethyl) and 3,3,3’-tris(2-hydroxyethyl) derivatives of 1,1’-[methylenebis(oxy)]bis(triaz-1-ene 2-oxides)

Synthetic procedures to access new potential NO donors that can generate NO in living systems, 3,3-bis(2-hydroxyethyl) and 3,3,3’-tris(2-hydroxyethyl) derivatives of 1,1’-[methylenebis(oxy)]bis(3,3-dialkyltriaz-1-ene 2-oxides), were elaborated. 3,3-Bis(2-acetoxyethyl)-1(chloromethoxy)triaz-1-ene 2-oxide reacts with 1-hydroxytriaz-1-ene 2-oxide sodium salts to give a series of alkylated 3,3-bis(2-acetoxyethyl) derivatives. Deacetylation of the latter produces 3-(2-hydroxyethyl)-11,11-dialkyl-6,8-dioxa-3,4,5,9,10,11-hexaazaundeca-4,9-dien-1-ol 4,10-dioxides and 11-alkyl-3-(2-hydroxyethyl)-6,8-dioxa-3,4,5,9,10,11-hexaazatrideca-4,9-diene-1,13-diol 4,10-dioxides.

Synthesis of 1-alkoxy-3-(2-hydroxyethyl)-1-triazene 2-oxides

Synthetic procedure to access the first representatives of a new series of 3-monosubstitued functional derivatives of 1-alkoxy-1-triazene 2-oxides, i.e., 1-alkoxy-3-(2-hydroxyethyl)- and 1-alkoxy-3-(2-acetoxyethyl)-1-triazene 2-oxides, were elaborated. 1-Alkoxy-3,3-bis(2-hydroxyethyl)-1-triazene 2-oxides were used to derive 3-(2-acetoxyethyl)-, 3-(2-bromoethyl)- and 3-(2-cyanoethyl)substituted 1-alkoxy-3-(2-acetoxyethyl)-1-triazene 2-oxides.

Nitro-substituted bis(methyl- ONN -azoxyfurazanyl)furoxans

Reaction of bis(aminofurazanyl)furoxan with 2,2-dimethyl-5-nitro-5-nitroso-1,3-dioxane in the presence of dibromoisocyanurate and a series of subsequent transformations give rise to the following bis(mononitroalkyland polynitromethyl-ONN-azoxyfurazanyl)furoxans: bis(nitromethyl-ONN-azoxyfurazanyl)furoxan, bis(dinitromethyl-ONN-azoxyfurazanyl)furoxan, bis(trinitromethyl-ONN-azoxyfurazanyl)furoxan, and a number of their derivatives, including bis(fluorodinitrometyl-ONN-azoxyfurazanyl)furoxan.