4-alkyl-6-amino-4-N 3,N 5-diaryl-2-thioxo-1,2,3,4-tetrahydropyridine-3,5-dicarboxamides: I. Tandem synthesis and alkylation. Molecular and crystal structure of 6-allylsulfanyl-2-amino-4-isobutyl-N 3,N 5-di-m-tolyl-3,4-dihydropyridine-3,5-dicarboxamide

4-Alkyl-6-amino-4-N ³,N ⁵-diaryl-2-thioxo-1,2,3,4-tetrahydropyridine-3,5-dicarboxamides were obtained via tandem synthesis involving the Knoevenagel reaction, Michael reaction and intramolecular condensation. Alkylation of the obtained dicarboxamides proceeds regioselectively at the S atom to form the corresponding thioethers. Structure of 6-allylsulfanyl-2-amino-4-isobutyl-N ³,N ⁵-di-m-tolyl-3,4-dihydropyridine-3,5-dicarboxamide was uniquely determined by XRD analysis.     

Synthesis and Crystal Structure of 3-Carbamoyl-6-methyl-5-phenylcarbamoyl-2-thioxo-1,2,3,4-tetrahydropyridine-4-spirocyclohexane

3-Carbamoyl-6-methyl-5-phenylcarbamoyl-2-thioxo-1,2,3,4-tetrahydropyridine-4-spirocyclohexane has been synthesized by the condensation of cyclohexylidenecyanothioacetamide with acetoacetanilide and piperidine. The structure of the product was established by X-ray structural analysis.     

Synthesis of N,6-diaryl-4-methyl-2-thioxo-1,2,3,6-tetrahydropyrimidine-5-carboxamides

Russian Journal of Organic Chemistry -     

Synthesis of new 2-thioxo-1,2,3,4-tetrahydropyridine-3-carboxanilides and their alkylation

2-Thioxo-1,2,3,4-tetrahydropyridine-3-carboxanilides were obtained by the reaction of α,β-unsubstituted ketones with 2-thioxocarbamoylacetanilide and their alkylation was studied. Structure of 3-allyl-4,6-diphenyl-2-thioxo-1,2,3,4-tetrahydropyridine-3-carboxanilide was proved by the X-ray diffraction method.     

Synthesis, properties, and structures of ammonium 4-aryl-5-cyano-2-oxo-1,2,3,4-tetrahydropyridine-6-thiolates

The reaction of arylcyanomethylenethiocetamides with Meldrum, acid gave Michael adducts as ammonium salts. When heated in alcohol, these salts undergo cyclization to ammonium 4-aryl-5-cyano-2-oxo-1,2,3,4-tetrahydropyridine-6-thiolates. The structure ofN-methylmorpholinium 4-(2′-chlorophenyl)-5-cyano-2-oxo-1,2,3,4-tetrahydropyridine-6-thiolate was established by X-ray structural analysis. Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 5, pp. 1029–1034, May, 1997.     

N-Methylmorpholinium 4-aryl-5-cyano-3-methoxycarbonyl-2-oxo-1,2,3,4-tetrahydropyridine-6-thiolates: synthesis and properties

Reactions of aromatic aldehydes with cyanothioacetamide and dimethyl malonate in the presence ofN-methylmorpholine affordedN-methylmorpholinium 4-aryl-5-cyano-3-methoxycarbonyl-2-oxo-1,2,3,4-tetrahydropyridine-6-thiolates. The latter were used to synthesize substituted 6-(alkylthio)-2-oxo-1,2,3,4-tetrahydropyridines. Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 485–487, March, 2000.     

Synthesis of N,6-diaryl-2-imino-4-methyl-3-cyano-1,2,3,6-tetrahydropyrimidine-5-carboxamides

Russian Journal of General Chemistry -     

Synthesis and alkylation ofN-methylmorpholinium 5-cyano-4-(3- and 4-hydroxyphenyl)-2-oxo-1,2,3,4-tetrahydropyridine-6-thiolates

The reactions of 3- or 4-hydroxybenzaldehydes with cyanothioacetamide and Meldrum's acid in the presence ofN-methylmorpholine affordedN-methylmorpholinium 5-cyano-4-(3-or 4-hydroxyphenyl)-2-oxo-1,2,3,4-tetrahydropyridine-6-thiolates, respectively. The resulting compounds were used in the synthesis of substituted 6-alkylthio-1,2,3,4-tetrahydropyridin-2-ones. Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 12, pp. 2333–2336. December, 1999.     

Synthesis of N 3,N 5,4-triaryl-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxamides

Russian Journal of Organic Chemistry -     

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 structure of N,6-diaryl-4-methyl-2-cyanoimino-1,2,3,6-tetrahydropyrimidine-5-carboxamides

Russian Journal of General Chemistry - Reactions of acetoacetic acid N-arylamides with aromatic aldehydes and cyanoguanidine have led to the formation of...     

Synthesis and reactions of 1-R-3-benzoyl-5-ethoxycarbonyl-6-oxo-1,2,3,6-tetrahydropyridine-2-thiones

Cycloacylation of N-R-3-oxo-3-phenylpropanethioamides by diethyl ethoxymethylenemalonate occurs selectively to form 1-R-3-benzoyl-5-ethoxycarbonyl-6-oxo-1,2,3,6-tetrahydropyridine-2-thiones which are convenient starting materials for the synthesis of bi-and tricyclic hetero systems including the previously unknown 9-R-7-ethoxycarbonyl-5-phenyl-8,9-dihydropyrido[2,3-d][1,2,4]triazolo[1,5-a]-pyrimidin-8-ones. __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1660–1669, November, 2007.     

Synthesis and alkylation of n<Subscript>(3)</Subscript>-aryl-n<Subscript>(5)</Subscript>-phenyl-6-amino-4-aryl(2-furyl)-2-thioxo-1,2,3,4-tetrahydropyridine-3,5-dicarboxamide

N₍₃₎-Aryl-N₍₅₎-phenyl-6-amino-4-aryl(2-furyl)-2-thioxo-1,2,3,4-tetrahydropyridine-3,5-dicarboxamides have been obtained by the interaction of N-phenyl-3-aryl(2-furyl)-2-cyanoacrylamides with 3-amino-3-thioxopropananilides under the conditions of the Michael reaction. N₍₃₎-Aryl-N₍₅₎-phenyl-2-alkylthio-6-amino-4-aryl(2-furyl)-3,4-dihydropyridine-3,5-dicarboxamides and N₍₃₎, N₍₅₎-diphenyl-6-benzylthio-4-(2-furyl)-2-oxo-1,2,3,4-tetrahydropyridine-3,5-dicarboxamides were synthesized by alkylation of the products. __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 1018–1023, July, 2008.     

2-氨基-N,3-二甲基-5-硫氰基苯甲酰胺的合成

本文报道一种未见文献报道的化合物2-氨基-N,3-二甲基-5-硫氰基苯甲酰胺的合成。从3-甲基氨茴酸出发,用两种不同方法得到2-氨基-N,3-二甲基苯甲酰胺,随后在0-5℃条件下与硫氰酸钠与溴素的混合物反应,高收率地得到2-氨基-N,3-二甲基5-硫氰基-苯甲酰胺。该化合物经核磁共振氢谱、碳谱、红外光谱和高分辨质谱表征和确认。同时考察了硫氰酸钠与溴素的用量及比例对反应产物纯度和收率的影响,发现2-氨基-N,3-二甲基苯甲酰胺、硫氰酸钠与溴素的摩尔比为1∶4∶2时,能以好的分离收率得到目标产物。     

Synthesis of 3-cyano-4, 6-diaryl-3, 4-dihydropyridine-2-thionks

3-Cyano-4, 6-diaryl-3, 4-dihydropyridine-2-thiones have been synthesized for the first time by the condensation of arylideneacetophenones or 1-piperidino-1-phenyl-2-benzoylethane with cyanothioacetamide and the 1, 1-dicyano-2-aryl-3-benzoylpropane with hydrogen sulfide in the presence of bases. It has been established by PMR spectroscopy that 3-cyano-3,4-dihydropyridine-2-thiones exist in solutions in the form of mixture of cis and trans isomers.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1515–1520, November, 1983.     

Synthesis and exchange reactions of 5-alkyl-2-oxo-6-thioxo-1,2,3,6-hexahydropyrimidine-4-carboxylic acids

An improved preparation of 2-oxo-6-thioxo-1,2,3,6-hexahydropyrimidine-4-carboxylic acid 3, a potent inhibitor of dihydroorotase is presented. Trans-5-alkyl-2-oxo-6-thioxohexahydropyrimidine-4-carboxylic acids 12a-c were synthesised via the thiation of the p-methoxybenzyl esters of 5-alkyldihydroorotic acids with Lawesson's reagent followed by subsequent de-protection. The corresponding cisisomers were prepared by reduction of 5-alkyl-6-thioxoorotic acids with zinc in acetic acid. The stability and exchange reactions of 12a-c under physiological conditions were investigated by ultra-violet and ¹H nmr spectroscopy. The attempted synthesis of 16 , a fused cyclopentyl derivative of 3 is also presented.     

Domino reactions of 1,2-diimidoyl-1,2-dichloroethanes. Synthesis of 3-imino-1,2-dithia-3h-cyclopent-4-enes, 3-amino-2-thioxo-2,5H-pyrrol-5-ones, 2,3-diamino-4-thioxo-4H-thiopyrans, and 6-imino-6H-1,3-oxazines

The reaction of mono- and dilithiated ethyl thioglycolate with 1,2-diimidoyl-1,2-dichloroethanes, aza-analogues of oxalyl chloride, afforded (depending on the reaction conditions) 3-imino-1,2-dithia-3H-cyclopent-4-enes, 3-amino-2-thioxo-2,5H-pyrrol-5-ones, and 2,3-diamino-4-thioxo-4H-thiopyrans. The reaction of the dianion of ethyl hippurate with 1,2-diimidoyl-1,2-dichloroethanes afforded 6-imino-6H-1,3-oxazines.