Synthesis of 1,2,4-triazole-3-thiols and their S-substituted derivatives

New 1,2,4-triazole-3-thiols were synthesized by reactions of the corresponding carboxylic acid hydrazides with isothiocyanates and subsequent cyclization of intermediate 1,4-substituted thiosemicarbazides. Alkylation of 1,2,4-triazole-3-thiols with benzyl chlorides and bromacetophenones gave only S-substituted derivatives.     

On the use of isotopic species in determing the parameters of intensity theory in the vibrational spectra of polyatomic molecules

The problem of determining the true sign combinations of the derivatives of dipole moment and polarizability of molecules in the normal coordinates was investigated. It was shown that the use of spectral data on isotopic species allows us to reduce the number of possible sign combinations of these derivatives to two.     

Application of Suzuki-Miyaura Reaction in the Chemistry of Oxolan-2-ones

Russian Journal of Organic Chemistry - The reactions of 2-(2-chloroprop-2-en-1-yl)-5,5-dimethyloxolan-2-one with arylboronic acids in the presence of Pd(PPh3)4 and K2CO3 was used to synthesize...     

New Synthesis of 2-Acetonyl-4-alkoxymethylbutanolide

A new method was developed for synthesis of 2-acetonyl-4-alkoxymethylbutanolides by treatment of 4-alkoxymethyl-2-(-chloroallyl)butanolides with concentrated sulfuric acid and subsequent hydrolysis. 4-alkoxymethyl-2-(-chloroallyl)butanolides are readily obtained by alkylation of accessible 4-alkoxymethyl-2-ethoxycarbonylbutanolides with 2,3-dichloropropene, followed by hydrolysis and decarboxylation of the resulting 4-alkoxymethyl-2-(-chloroallyl)-2-ethoxycarbonylbutanolides.     

Synthesis and Some Transformations of 4-Alkoxymethyl-2-ethoxycarbonyl-2-ethoxycarbonylmethylbutanolides

A method was developed for the production of 4-alkoxy-2-ethoxycarbonyl-2-ethoxycarbonylmethylbutanolides. The latter were subjected to alkaline and acid hydrolysis, leading to 4-alkoxymethyl-2-carboxymethylbutanolides, from which lactone-containing thioureas and amides of carboxylactones with novel structures were obtained. __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1625–1633, November, 2005.     

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 Some Transformations of Ethyl 5-Alkoxymethyl-3-(2-methyl-3-oxobutyl)-2-oxotetrahydrofuran-3-carboxylates

Michael reaction of ethyl 5-alkoxymethyl-2-oxotetrahydrofuran-3-carboxylates with 3-methyl-3-buten-2-one gave ethyl 5-alkoxymethyl-3-(2-methyl-3-oxobutyl)-2-oxotetrahydrofuran-3-carboxylates. Alkaline hydrolysis of the latter, followed by decarboxylation afforded 5-alkoxymethyl-3-(2-methyl-3-oxobutyl)tetrahydrofuran-2-ones. The bromination of ethyl 5-alkoxymethyl-3-(2-methyl-3-oxobutyl)-2-oxotetrahydrofuran-3-carboxylates provides a convenient method for the preparation of 3-acetyl-8-alkoxymethyl-3-methyl- and 8-alkoxymethyl-3-bromoacetyl-3-methyl-2,7-dioxaspiro[4.4]nonane-1,6-diones in high yields.     

Synthesis of Carboxylactones and New Heterocyclic Compounds

The Michael reaction of 2‐ethoxycarbonyl‐4‐alkoxymethylbutanolides with methyl acrylate affords esterolactones in high yields. Alkaline hydrolysis of the latter resulted in carboxylactones that were transformed into ethyl α‐bromolactonoesters. The reactions of the latter with thiourea and arylthioureas result in heterocyclic compounds of an original structure joint with a butanolide ring.     

Synthesis of new α-spiroheteryl-fused butanolides

4-Alkoxymethyl-2-bromo-2-ethoxycarbonylbutanolides were obtained with good yields by the bromination of 4-alkoxymethyl-2-ethoxycarbonylbutanolides with bromine in dry carbon tetrachloride. Reaction of the products with thiourea and aryl-substituted thioureas gave spiroheteryl-fused lactones of a new generation-8-alkoxymethyl-3-amino(arylamino)-7-oxa-4-thia-2-azaspiro[4,4]-2-nonene-1,6-diones. __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 510–514, April, 2006.     

Synthesis of 2-substituted aminothiazol-4(5<Emphasis Type="Italic">H</Emphasis>)-ones proceeding from carboxylactones

New representatives of 2,2,4-trisubstituted butano-4-lactones were synthesized. By a series of transformations the corresponding γ-carboxylactones were obtained. The latter served as starting compounds for preparation of heteryl-linked lactones, 5-[5-{(alkoxymethyl)-2-oxotetrahydrofuran-3-yl}methyl]-2-arylaminothiazol-4(5H)-ones.