Synthesis and study of tautomeric properties of 2-(5-R-2-furyl)thiazolin-4-ones

Compounds were synthesized by reaction of 5-R-2-cyanofurans with thioglycolic acid, which, according to IR, PMR, and mass spectrometric data, exist in the form of two tautomers, 4-hydroxythiazole and thiazolin-4-one.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 404–409, March, 1987.     

Synthesis and reactivity of thieno[2,3-<Emphasis Type="Italic">b</Emphasis>]pyridine-2,3-diamines

It has been established that the interaction of N¹-(2-hydroxyphenylmethylthieno[2,3-b]pyrid-3-yl)arylamides with hydrazine hydrate leads to thieno[2,3-b]pyridine-2,3-diamines. It was shown that the reaction of the latter with acetylacetone and acetoacetic ester occurs regioselectively at the amino group in position 3 of the thiophene ring. __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1400–1408, September, 2007.     

Amidine tautomerism in the 1,3-diacyl-2-(5-substituted furfuryl)thiourea series. Molecular structure of 1,3-diacetyl-2-(5-ethoxycarbonylfurfuryl)thiourea

The effect of substituents in the furan ring on the dynamics of amidine tautomerism in 1,3-diacetyl-2-(5-R-furfuryl)thioureas is demonstrated. The conformation of 1,3-diacetyl-2-(5-ethoxycarbonylfurfuryl)thiourea was established by x-ray diffraction analysis.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 741–745, June, 1991.     

Polyfuryl(aryl)alkanes and their derivatives. 13. Molecular structure of bis(5-methyl-2-furyl)(4-methoxyphenyl)methane and tris(5-methyl-2furyl)methane

4-Methoxyphenylbis(5-methyl-2-furyl)methane (I) and tris(5-methyl-2-furyl)methane (II) were investigated by x-ray crystallographic analysis. It was established that the molecules of (I) have a propeller conformation with C_s symmetry, and the furan rings are turned with the oxygen atoms towards the methine hydrogen atom. The molecule of (II) has a different conformation with C_2v symmetry; one of the furan rings and the methine C-H bond lie ideally in one plane, and the other two furan rings are arranged symmetrically with the oxygen atoms in relation to this bond and incline toward eclipsing of the exocyclic C-C bond.For Communication 12, see [1].Kubansk State Technological University, Krasnodar. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 648–653, May, 1996.     

Synthesis and properties of 2-amino-5-(5-nitro-2-furyl) thiazole derivatives

The hydrochlorides of the corresponding 2-aminothiazoles, which were converted to the free bases, were obtained by hydrolysis of 2-acylamino-5-(5-nitro-2-furyl) thiazoles. Reactions that take place at the amino group of 2-amino-5-(5-nitro-2-furyl)thiazoles are described.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1038–1041, August, 1985.     

Synthesis of substituted benzoxazinylthieno[2,3-<Emphasis Type="Italic">b</Emphasis>]pyridines by the reaction of (3-cyanopyridin-2-ylthio)acetic acids or their amides with <Emphasis Type="Italic">o</Emphasis>-aminophenyl(diphenyl)carbinol

A general method for the synthesis of 3-amino-2-(4,4-diphenyl-4H-3,1-benzoxazin-2-yl)thieno[2,3-b]pyridines was proposed. The method involves reactions of (3-cyanopyridin-2-ylthio)acetic acids or their amides with o-aminophenyl(diphenyl)carbinol in nitromethane in the presence of perchloric acid followed by neutralization of the resulting salts.__________Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 12, pp. 2759–2762, December, 2004.     

Synthesis and some transformations of new 9-furylnaphtho[2,3-b]furan derivatives

The synthesis of a number of naphtho[2,3-b]furan derivatives, containing a furyl substituent in position 9 by intramolecular cyclization of 2-carboxy and 2-formylbis(5-alkylfur-2-yl)methanes is described. The reactivity of the title compounds in formylation, acetylation, nitration, and oxidation reactions has been investigated. It was shown that nitration of 2-methyl-9-(5-methyl-2-furyl)naphtho[2,3-b]furan-4-yl acetate leads to oxidative furan ring opening rather than to electrophilic substitution.     

Quantum chemical calculations of hydration electrostatics and electrochemical oxidation potential of cyclic nitroxide radicals

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Phenylfurylthieno[2,3-<Emphasis Type="Italic">b</Emphasis>]pyridyl-methanes. synthesis and reactions of the furan ring transformation

Triarylmethane derivatives with various substituents, phenyl, 5-methyl-2-furyl, and 3-acylamino-thieno[2,3-b]pyrid-2-yl have been obtained for the first time. The behavior of these compounds under protolytic conditions has been studied. It was shown that the character of the protection of the amino group of the thienopyridine fragment affects the type of transformation of the furan ring.