Synthesis and transformations of 6-amino-3,5-dicyano-4ethylpyridine-2(1H)-thione

The condensation of propionaldehyde with cyanothioacetamide gives 6-amino-3,5-dicyano-4-ethylpyridine-2(1H)-thione, which was used to obtain substituted 2-alkylthiopyridines, 2-ethylthio-6- ethylaminopyridine, and pyrazolo[3,4-b]pyridine.T. G. Shevchenko Lugansk State Pedagogical Institute, 348011 Lugansk. N. D. Zelinskii Institute of Organic Chemistry, Russian Academy of Science, 117913 Moscow. Translated from Khimiya Geterotsklicheskikh Soedinenii, No. 8, pp. 1094–1098, August, 1996. Original article submitted March 4, 1996; revision submitted July 1, 1996.     

Synthesis and structure of 6-amino-3,5-dicyano-4-heptylpyridine-2(1H)-thione

Condensation of caprylic aldehyde with cyanothioacetamide taken in a ratio of 1:2 affords 6-amino-3,5-dicyano-4-heptylpyridine-2(1H)-thione. The structure of the thione was studied by X-ray structural analysis. Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 196–198, January, 1997.     

Synthesis of 2,6-diamino-3,5-dicyano-4-ethyl-4H-thiopyran and its recyclization to 6-amino-3,5-dicyano-4-ethylpyridine-2(1H)-thione

The triple condensation of propionaldehyde, malononitrile, and cyanothioacetamide gives 2,6-diamino-3,5-dicyano-4-ethyl-4H-thiopyran, which recyclizes to give 6-amino-3, 5-dicyano-4-ethylpyridine-2(1H)-thione. This thione was used to synthesize substituted 2-alkylthiopyridines and the corresponding thieno[2,3-b]pyridines.T. G. Shevchenko Lugansk State Pedagogical Institute, 348011 Lugansk. N. D. Zelinski Institute of Organic Chemistry, Russian Academy of Sciences, 117913 Moscow. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1099–1103, August, 1996. Original article submitted May 13, 1996.     

Synthesis and alkylation ofN-methylmorpholinium 6-amino-3,5-dicyano-4-methylpyridine-2-thiolate

The condensation of acetaldehyde with a twofold excess of cyanothioacetamide andN-methylmorpholine givesN-methylmorpholinium 6-amino-3,5-dicyano-4-methylpyridine-2-thiolate. This compound is also formed by recyclization of 2,6-diamino-3,5-dicyano-4-methyl-4H-thiopyran. From this pyridinethiolate, several substituted 2-alkylthiopyridines and 3,6-diamino-5-cyano-4-methyl-2-methoxycarbonylthieno[2,3-b]pyridine were obtained.     

Synthesis and properties ofN-methylmorpholinium 6-amino-3,5-dicyano-1,4-dihydropyridine-4-spirocyclopentane-2-thiolate

The reaction of cyclopentylidenecyanothiocetamide with cyanothioacetamide andN-methylmorpholine gaveN-methylmorpholinium 6-amino-3,5-dicyano-1,4-dihydropyridine-4-spirocyclopentane-2-thiolate, which was used in the syntheses of substituted 2-alkylthiodihydropyridines and pyrazolodihydropyridine. Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 10, pp. 1849–1851, October. 1997.     

1-(2-氨基-3,5-二氰基-4-芳基-4H-吡喃-6-基)愈创兰烃薁的合成

在醋酸铵作用下,通过1-氰乙酰基愈创兰烃薁、芳香醛、丙二腈的三组分反应,一锅法合成了一系列1-(2-氨基-3,5-二氰基-4-芳基-4H-吡喃-6-基)愈创兰烃薁衍生物.该反应操作简单、条件温和、收率良好.产物结构经NMR,MS,IR及元素分析等得以证实.     

Multicomponent synthesis of 2-alkylthio-6-amino-3,5-dicyano-1,4-dihydropyridine-4-spirocycloalkanes. Molecular and crystal structure of 6-amino-2-(2-methylbenzylthio)-3,5-dicyano-1,4-dihydropyridine-4-spirocyclopentane

2-Alkylthio-6-amino-3,5-dicyano-1,4-dihydropyridine-4-spirocycloalkanes were synthesized via the reaction of cycloalkylidene malononitriles with cyanothioacetamide and alkyl halides. The structure of 6-amino-2-(2-methylbenzylthio)-3,5-dicyano-1,4-dihydropyridine-4-spirocyclopentane was determined by the X-ray diffraction analysis.     

The use of aliphatic aldehydes for the synthesis of 4-alkyl-6-amino- 3,5-dicyanopyridine-2(1H)-thiones

The condensation of aliphatic aldehydes with malononitrile and cyanothioacetamide gives 4-alkyl-2,6-diamino-3,5-dicyano-4H-thiopyrans which recyclize into 4-alkyl-6-amino3,5-dicyanopyridine-2(IH)-thiones. The latter are easily S-alkylated with -haloacetonitriles and -haloacetophenones.Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 4, pp. 938–942, April, 1996     

Synthesis of 2-amino-4,5-disubstituted 3,5-dicyano-4,5-dihydrofurans

A new reaction was found for the preparation of difficult-to-obtain polyfunctional dihydrofurans, viz., the reaction of tetracyanoethylated ketones with hydrogen peroxide in the presence of a base.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1027–1030, August, 1985.     

An approach to acyclo-3-deazapyrimidine S-nucleosides via 3,5-dicyano-2(1H)-pyridinethiones

A series of different acyclo-3-deazapyrimidine nucleosides have been synthesized. The site of glycosylation was confirmed by ¹³C NMR spectroscopy.     

New method for the synthesis of 6-amino-4-aryl-3,5-dicyano-3,4-dihydropyridine-2(1H)-thiones by recyclization of 4-aryl-2,6-diamino-4H-thiopyranes

Ammonium 6-amino-4-aryl-3,5-dicyano-1,4-dihydropyridine-2-thiolates were synthesized by recyclization of 4-aryl-2,6-diamino-3,5-dicyano-4H-thiopyranes in the presence of organic bases. On acidification of the products, the corresponding substituted 3,4-dihydropyridine-2(1H)-thiones were obtained which were used in the synthesis of 2-alkylthio-1,4-dihydropyridines, bis-(pyridyl-2)disulfides and thieno[2,3-b]pyridines.Deceased.T. G. Shevchenko Lugansk State Pedagogical Institute, Lugansk 348011. N. D. Zelinskii Institute of Organic Chemistry, Russian Academy of Sciences, Moscow 117913. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 909–914, July, 1997.     

Synthesis of 4-amino-6-chloro-1,3,5-triazin-2(1H)-ones

Conditions for selective substitution for one chlorine atom in 2-(R,R??-amino)-4,6-dichloro-1,3,5-triazines with a hydroxide ion were elaborated. Spectral and calculation methods showed that the products formed are in the lactam form, i.e., have the structure of 4-chloro-6-(R,R??-amino)-1,3,5-triazin-2(1H)-ones.     

Synthesis of 4-Acyl-2-amino-6-(arylsulfanyl)pyridine-3,5-dicarbonitriles

Russian Journal of Organic Chemistry - The reaction of 4-acyl-2-amino-6-chloropyridine-3,5-dicarbonitriles with aromatic thiols in 1,4-dioxane in the presence of triethylamine led to the formation...     

Michael reaction in synthesis of 6-amino-4-(4-butoxyphenyl)-3,5-dicyanopyridine-2(1H)-thione

The reaction of 4-butoxybenzalcyanoacetic ester with cyanothioacetamide yielded 6-amino-4-(4-butoxyphenyl)-3,5-dicyanopyridine-2(1H)-thione, also synthesized by recyclization of 2,6-diamino-4-(4-butoxyphenyl)-3,5-dicyano-4H-thiopyran and condensation of 4-butyoxybenzaldehyde with a two-fold excess of cyanothioacetamide. Substituted 2-alkylthiopyridines and thieno[2,3-b]pyridines were obtained with the indicated pyridinethione. T. G. Shevchenko Lugansk State Pedagogical Institute, Lugansk 348011. Ukraine, N. D. Zelinskii Institute of Organic Chemistry, Russian Academy of Sciences, Moscow 117913, Russia. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 213–219, February, 1998.     

Synthesis,alkylation, and molecular and crystal structure ofN-methylmorpholinium 6-amino-3,5-dicyano-1,4-dihydropyridine-4-spirocyclohexane-2-thiolate

The reaction of cyano(cyclohexylidene)thioacetamide with cyanothioacetamide or malononitrile andN-methylmorpholine yieldsN-methylmorpholinium 6-amino-3,5-dicyano-1,4-dihydropyridine-4-spirocyclohexane-2-thiolate. Its structure was established based on the results of alkylation and X-ray structural analysis.Deceased.Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 10, pp. 2535–2540, October, 1996.     

One-Pot Synthesis of 6-Alkyl-4-amino-2-bromopyridine-3,5-dicarbonitriles

Russian Journal of Organic Chemistry - A one-pot procedure has been proposed for the synthesis of 6-alkyl-4-amino-2-bromopyridine-3,5- dicarbonitriles by reaction of malononitrile dimer with...     

Synthesis and properties of triethylammonium 4-aryl(hetaryl)-3,5-dicyano-6-oxo-1,4,5,6-tetrahydro-pyridine-2-selenolates

The reaction of (hetero)aromatic aldehydes, cyanoselenoacetamide, and 1-(cyanoacetyl)-3,5-dimethyl-pyrazole in the presence of triethylamine gives a mixture of the cis and trans diastereomers of triethylammonium 4-aryl(hetaryl)-3,5-dicyano-6-oxo-1,4,5,6-tetrahydropyridine-2-selenolates. The selenolates obtained react with alkyl halides to form the corresponding selenides.     

Synthesis of 1-alkyl-5-phenyl-4(1H)pyrimidinones

1-Alkyl-5-phenyl-4(1H)pyrimidinones are readily synthesized by condensing β-(dimethylamino)-N-[(dimethylamino)methylene] atropamides with methyl or ethyl amine. The latter compounds are prepared from phenylacetamides and dimethylformamide dimethyl acetal.