A. S. Galstyan

Syntheses on the Basis of 4-(Oxiran-2-ylmethyl)morpholine

Abstract4-(Oxiran-2-ylmethyl)morpholine was synthesized and converted into new morpholino derivatives of propan-2-ols and butan-4-olides.

Synthesis of N-aryl derivatives of vicinal aminoalcohols

Synthesis was performed of substituted 2-propanols based on glycidyl phenyl and glycidyl allyl ethers, Also some acetic acid esters were prepared.

Synthesis of new 3-phenoxypropan-2-ols with various heterocyclic substituents

Abstract1-Phenoxy-3-piperidinopropan-2-ol, 1-(5-methyl-1,3-benzothiazol-2-ylsulfanyl)-3-phenoxypropan-2-ol, 1-(2-hydroxy-3-phenoxypropyl)azepan-2-one, 1,1′-(6-chloro-1,3-benzothiazol-2-ylimino)bis(3-phenoxypropan-2-ol), 1-(1,3-benzothiazol-2-ylsulfanyl)-3-phenoxypropan-2-ol, 1,1′-(piperazine-1,4-diyl)bis(3-phenoxypropan-2-ol), and 1,3-bis(2-hydroxy-3-phenoxypropyl)barbituric acid were synthesized by condensation of 1,2-epoxy-3-phenoxypropane with the corresponding amines and thiols.

Syntheses proceeding from N-(oxiran-2-ylmethyl)-N-ethylaniline

The preparation of N-(oxiran-2-ylmethyl)-N-ethylaniline was developed. The compound was used in the synthesis of new N-derivatives of aromatic amines containing vicinal aminoalcohol moieties.

Syntheses on the Basis of Diethyl (2-Morpholinoethyl)malonate

New functionally substituted butan-4-olides were synthesized by reactions of diethyl (2-morpholinoethyl) malonate with 2-(allyloxymethyl)oxirane, 4-(oxiran-2-ylmethyl)morpholine, N-ethyl-N-(oxiran-2-ylmethyl)aniline, and 1-chloro-2,3-epoxypropane. 5-[2-(Morpholino)ethyl]barbituric and -thiobarbituric acids were also synthesized.

Sonogashira reaction of 5-substituted 3-(prop-2-yn-1-yl)oxolan-2-ones

Palladium-catalyzed cross-coupling of 5-methyl- and 5,5-dimethyl-3-(prop-2-yn-1-yl)oxolan-2-ones with dihaloarenes (dihaloheteroarenes) gave mixtures of the corresponding mono- and bis-coupling products. The latter can be obtained as the major products by variation of the catalytic system.

Synthesis and transformations of 5,5-disubstituted 3-alkenyloxolan-2-ones

By alkylation of 4,4-disubstituted 2-(ethoxycarbonyl)butanolides new 4,4-disubstituted 2-alkenyl-2-(ethoxycarbonyl)butanolides were synthesized, which at alkaline hydrolysis formed 4,4-disubstituted 2-alkenylbutanolides. By oxidation of the latter with hydrogen peroxide and formic acid diololactones were obtained that in conditions of pinacol-pinacolone rearrangement and oxidation with lead tetraacetate afforded formyl- and epoxybutanolides of new structure.

Synthesis of sulfur-containing vicinal aminoalcohols on the basis of N-(oxiran-2-ylmethyl)amines

The reaction of (methanediyldibenzene-4,1-diyl)dimethanethiol, (oxydibenzene-4,1-diyl)dimethanethiol, biphenyl-4,4′-diyldimethanethiol with 1-(oxiran-2-ylmethyl)piperidine and N-(oxiran-2-ylmethyl)-N-ethylaniline afforded the corresponding sulfur-containing vicinal aminoalcohols resulting from the opening of the oxirane ring in keeping with Krasusky rule.

Reactions of Aromatic Dithiols with Diethyl 2-Alkyl-2-(oxiran-2-ylmethyl)malonates

New sulfur-containing butano-4-lactones were synthesized by reaction of diethyl 2-alkyl-2-(oxiran-2-ylmethyl)malonates with biphenyl-4,4′-dithiol, (biphenyl-4,4′-diyl)dimethanethiol, and (2,4,6-trimethylbenzene-1,3-diyl)dimethanethiol. Opening of the oxirane ring in the initial ester followed the Krasuskii rule.