111853-33-9

Upstream product

• 110-89-4 piperidine 
• 7357-70-2 Cyanothioacetamide 
• 144-48-9 iodacetamide 
• 15802-62-7 (Z)-ethyl 2-benzylidenacetoacetate 
• 97651-04-2 6-methyl-4-phenyl-5-ethoxycarbonyl-3-cyano-3,4-dihydropyridine-2(1H)-thione 
• 620-80-4 ethyl 2-benzylidene acetoacetate 
• 111835-46-2 piperidinium salt of 6-methyl-4-phenyl-5-ethoxycarbonyl-3-cyano-1,4-dihydropyridine-2(1H)-thiol 

Downstream Products

• 111853-32-8 2-cyanomethylthio-6-methyl-4-phenyl-5-ethoxycarbonyl-3-cyano-1,4-dihydropyridine 
• 111853-37-3 3-amino-6-methyl-4-phenyl-5-ethoxycarbonyl-2-carbamoyl-4,7-dihydrothieno<2,3-b>pyridine 
• 111853-41-9 (3-cyano-5-ethoxycarbonyl-6-methyl-4-phenyl)pyridin-2-ylthioacetamide 
• 111853-40-8 2-cyanomethylthio-6-methyl-4-phenyl-5-ethoxycarbonyl-3-cyanopyridine 
• 111853-42-0 3-amino-6-methyl-4-phenyl-5-ethoxycarbonyl-2-cyanothieno<2,3-b>pyridine 
• 111853-36-2 3-amino-6-methyl-4-phenyl-5-ethoxycarbonyl-2-cyano-4,7-dihydrothieno<2,3-b>pyridine 
• 111853-43-1 3-amino-5-ethoxycarbonyl-6-methyl-4-phenylthieno[2,3-b]pyridine-2-carboxamide 

Relevant academic research and scientific papers

Synthesis, structure, and electrochemical characteristics of 4-aryl-2-carbamoylmethylthio-5-ethoxycarbonyl-1,4-dihydropyridine-3-carboxylic acid nitriles

We have obtained 4-aryl-2-carbamoylmethylthio-5-ethoxycarbonyl-1,4- dihydropyridine-3-carboxylic acid nitriles by S-alkylation of the corresponding 2-thioxo-1,2,3,4-tetrahydropyridine-3-carboxylic acid nitrile by iodoacetamide or one-pot multicomponent synthesis methods: condensation of 2-arylidene-acetoacetic acid ethyl ester, 2-cyanothioacetamide, piperidine, and iodoacetamide; acetoacetic acid ethyl ester, 3-aryl-2-cyanothioacrylamide, piperidine, and iodoacetamide; acetoacetic acid ethyl ester, an aromatic aldehyde, 2-cyanothioacetamide, piperidine, and iodoacetamide. We have carried out a comparative analysis of the capability of 2-alkylthio-4-aryl-5- ethoxycarbonyl-1,4-dihydropyridine-3-carboxylic acid nitriles for electrochemical oxidation as a function of the electronic properties of the aryl substituent in the 4 position of the heterocycle and the 2-alkylthio substituent. X-ray diffraction data indicate the existence of a hydrogen bond between the C=O of the 2-carbamoylmethylthio substituent and the NH of the hydrogenated heterocycle, which explains the more facile oxidation of the studied compounds compared with 2-methylthio-substituted 1,4-dihydropyridines.

SYNTHESIS OF 3-AMINO-6-METHYL-5-ETHOXYCARBONYL-4,7-DIHYDROTHIENOPYRIDINE DERIVATIVES

The alkylation of piperidinium salts of substituted 1,4-dihydropyridine-2-thiols with chloroacetonitrile or iodoacetamide gave 2-cyanomethylthio- and 2-carbamoylmethylthio-substituted 6-methyl-4-aryl(pyridyl)-5-ethoxycarbonyl-3-cyano-1,4-dihydropyridines, which undergo intramolecular cyclization in basic media to give 3-amino-6-methyl-4-aryl(pyridyl)-5-ethoxycarbonyl-2-cyano(carbamoyl)-4,7-dihydrothienopyridines.