111853-34-0

Upstream product

• 144-48-9 iodacetamide 
• 111835-48-4 5-Cyano-6-mercapto-2-methyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3-carboxylic acid ethyl ester; compound with piperidine 
• 864546-77-0 5-Cyano-2-methyl-4-(3-nitro-phenyl)-6-thioxo-1,4,5,6-tetrahydro-pyridine-3-carboxylic acid ethyl ester 

Downstream Products

• 111853-38-4 3-Amino-2-carbamoyl-6-methyl-4-(3-nitro-phenyl)-4,7-dihydro-thieno[2,3-b]pyridine-5-carboxylic acid ethyl ester 

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.