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,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.     

Functionally-substituted Alkoxyethylenes in Reactions with Nucleophiles. Part I. Synthesis of Six-membered Heterocycles

Russian Journal of Organic Chemistry -     

Molecular and crystal structure of 1-methylmorpholinium 6-methyl-4-phenyl-3-cyano-5-ethoxycarbonyl-1,4-dihydro-2-pyridineselenolate

The structure of 1-methylmorpholinium 6-methyl-4-phenyl-3-cyano-5-ethoxycarbonyl-1,4-dihydro-2-pyridineselenolate was studied using x-ray diffraction analysis. It was found that the 1,4-dihydropyridine ring has a boat conformation, and the plane of the pseudoaxial phenyl substituent is perpendicular to the bottom of this boat. In the anion, the C–Se bond length, which is 1.882(2) Å, indicates that the negative charge is formally located on the Se atom. The anions and cations of the salt in the crystal are linked by intermolecular hydrogen bonds.A. N. Nesmeyanov Institute of Heteroorganic Compounds, Russian Academy of Sciences, Moscow 117813, Russia. T. G. Shevchenko Lugansk State Pedagogical Institute, Lugansk 348011, Ukraine. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 785–789, June, 1998.     

Synthesis and properties of N-methylmorpholinium 4aryl-6-methyl-5-phenylcarbamoyl-3cyano-1,4dihydropyridine-2-thiolates. Molecular and crystalline structure of 2allylthio-6-methyl-5-phenylcarbamoyl-4-(2chlorophenyl)-3-cyano-1,4-dihydropyridine

By the condensation of an aromatic aldehyde, the anilide of acetoacetic acid, cyanothioacetamide, and Nmethylmorpholine, substituted N-methylmorpholinium 1,4-dihydropyridine-2-thiolates have been synthesized and subsequently used in the synthesis of the corresponding thiones, 2-alkylthiopyridines, thieno[2, 3b]pyridines, and disulfides. X-ray diffraction has been used to establish the structure of 2-allylthio-6-methyl-5phenylcarbamoyl-4-(2-chlorophenyl)-3-cyano-1, 4-dihydropyridine.T. G. Shevchenko Lugansk State Pedagogical Institute, Lugansk 348011. A. N. Nesmeyanov Institute of Heteroorganic Compounds, Russian Academy of Sciences, Moscow 117813. N. D. Zelinskii Institute of Organic Chemistry, Russian Academy of Sciences, Moscow 117913. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1243–1251, September, 1996. Original article submitted May 13, 1996.     

Propanal in the Syntheses of Alkyl-substituted 3-Cyano-2-piperidone, 3-Cyano-2,5,6,7-tetrahydropyrindin-2(1H)-one, and 3-Cyanopyridine-2(1H)-thione

Condensation of propanal with cyanothioacetamide and morpholine gave 3-cyano-4-ethyl-5-methyl-6-morpholino-2-piperidone, the structure of which was studied by X-ray analysis. Reaction of propanal with cyanothioacetamides and cycloalkanone enamines gave 3-cyano-4-ethyl-2,5,6,7-tetrahydropyrindin-2(1H)-one and 3-cyano-4-ethyl-5,6-hexamethylenepyridine-2(1H)-thione. The latter was used for the preparation of substituted 2-benzyloxycarbonylmethylthiopyridine and 3-amino-2-benzyloxycarbonylthieno[2,3-b]pyridine. __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 1053–1059, July, 2005.     

Synthesis of Ammonium 5-Arylcarbamoyl-4-heteryl-6-methyl-3-cyano-1,4-dihydropyridine-2-thiolates and 4-Heteryl-5-carbamoyl-6-methyl-3-cyano-1,4-dihydropyridine-2-selenolates

The condensation of enamines derived from acetoacetanilides, heterocyclic aldehydes, and cyanothioacetamide yielded ammonium 5-arylcarbamoyl-5-heteryl-6-methyl-3-cyano-1,4-dihydropyridine-2-thiolates, which were subsequently used for the synthesis of substituted 2-alkylthio-1,4-dihydropyridines, 2-alkylthiopyridines, and thieno[2,3-b]pyridines. The reaction of acetoacetamide with heteroaromatic aldehydes and cyanoselenoacetamide in the presence of N-ethylmorpholine yielded N-ethylmorpholinium 4-heteryl-5-carbamoyl-6-methyl-3-cyano-1,4-dihydrolyridine-2-selenolates, from which substituted 2-alkylseleno-1,4-dihydropyridines were prepared.__________Translated from Zhurnal Obshchei Khimii, Vol. 75, No. 3, 2005, pp. 483–492.Original Russian Text Copyright © 2005 by Dyachenko.