M. M. Vartanyan

Synthesis of acetonylmalonaldehyde and its interaction with aminoazoles

Acetonylmalonaldehyde (1) was obtained for the first time by hydrolysis of 2,5-dimethoxy-5-methyltetrahydrofuran-3-carbaldehyde. The interaction of1 with 3-amino-5-methylpyrazole, 3-amino-1,2,4-triazole, 2-aminobenzimidazole, and 5-aminotetrazole results in the formation of functionally substituted azolopyrimidines.

HYDROFURANS IN THE SYNTHESIS OF HETEROCYCLES : A REVIEW

The use of hydrofurans in the synthesis of heterocyclic compounds is reviewed.

SYNTHESIS OF 2-(3-HYDROXYACETONYL)MALONIC ALDEHYDE AND ITS DERIVATIVES. THEIR REACTIONS WITH 5-AMINOTETRAZOLE

Abstract2-(3-Hydroxyacetonyl)malonic aldehyde and its derivatives were prepared for the first time by the hydrolysis of 2-substituted 2,5-dimethoxy-4-formyltetrahydrofuranes. Their interaction with 5-aminotetrazole gave functionally substituted 6-tetrazolo[1,5-a]pyrimidines.

Synthesis of ?-formyl-2,5-dialkoxytetrahydrofurans and their reaction with 3-amino-1,2,4-triazole

New β-formyl-2,5-dialkoxytetrahydrofurans were synthesized by hydroformylation of the corresponding 2,5-dihydrofurans. The aldehydes obtained react with 3-amino-1,2,4-triazole to give 6-(2-oxopropyl)-1,2,4-triazolo[1,5-a]pyrimidines.

Reaction of 3-formyl-2-methoxy-1,6-dioxaspiro[4.4]nonanes with 3-amino-1,2,4-triazole: synthesis of 2-(1,2,4-triazolo[1,5-a]pyrimid-6-yl)methylenetetrahydrofurans

The reaction of 3-formyl-2-methoxy-1,6-dioxaspiro[4.4]nonanes with 3-amino-1,2,4-triazole gives 2-(1,2,4-triazolo[1,5-a]pyrimid-6-yl)methylenetetrahydrofurans in 51–65% yields.

Synthesis of 2-substituted 3-formyl-5-methoxy-tetrahydrofurans from 2,5-dimethoxytetrahydrofuryl-3-carbinols

The acid-catalyzed rearrangement of 2,5-dimethoxytetrahydrofuryl-3-carbinol, obtained from 2,5-dimethoxy-3-formyltetrahydrofuran, gave the 2-substituted 3-formyl-5-methoxytetrahydrofuran.

Liquid-phase hydroformylation of 2,3- and 2,5-dihydrofurans

The synthesis of 3-formyl derivatives of the tetrahydrofuran series was carried out by hydroformylation of 2,3-dihydrofuran and 2,5-dimethoxy-2,5-dihydrofuran in the presence of HRh(CO)(PPh3)3. The influence of the temperature, pressure, catalyst concentration, and the nature of the solvent on the conversion of dihydrofuran, the composition of aldehydes obtained and the selectivity of their formation was investigated.

Catalytic hydroformamination of dihydrofurans

ConclusionsA preparative method has been developed for the synthesis of 3-(N-alkyliminomethyl)-tetrahydrofurans and 3-(N, N-dialylaminomethyl)tetrahydrofurans by the hydroformamination of 2,3- and 2,5-dihydrofurans in the presence of HRh(CO)(PPh3)3.

Investigation of the mass-spectrometric behavior of aminomethyl and aminomethylene derivatives of tetrahydrofuran

The principal pathway in the mass-spectrometric fragmentation of aminomethyl-tetrahydrofurans is cleavage of the α-C-C bond, in which a tetrahydrofuranyl radi cal is eliminated in the form of a neutral fragment, and the charge is retained on the amino fragment. This process is completely absent in methylene derivatives for which one of the characteristic fragmentation pathways is cleavage of the β bond with retention of the charge on the hydrofuran fragment. The established mass-spectrometric principles makes it possible to reliably distinguish amino-methyl- and aminomethylenetetrahydrofurans.

Synthesis and hydrogenation of acetonylmalonaldehyde bis(ethylene acetal)

A single-step synthetic route to acetonylmalonaldehyde bis(ethylene acetal) from 2,5-dimethoxy-5-methyltetrahydrofuran-3-carbaldehyde was proposed.