Direct Aminolysis of Ethoxycarbonylmethyl 1,4-Dihydropyridine-3-carboxylates
Copyright policy )Direct Aminolysis of Ethoxycarbonylmethyl 1,4-Dihydropyridine-3-carboxylates
The ethoxycarbonylmethyl esters of 1,4-dihydropyridines were directly converted into carbamoylmethyl esters in the presence of 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD) in good to excellent yields under mild conditions. The use of TBD is crucial for the successful aminolysis of ethoxycarbonylmethyl ester of 1,4-dihydropyridines with secondary amines as without it the reaction does not proceed at all. The aminolysis reaction proceeded regioselectively, as the alkyl ester conjugated with the 1,4-dihydropyridine cycle was not involved in the reaction. Screening of other N-containing bases, such as triethylamine (TEA), pyridine, 4-(N,N-dimethylamino)pyridine (DMAP), 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), 1,5-diazabicyclo[4.3.0]non-5-ene (DBN), imidazole, tetramethyl guanidine (TMG) and 7-methyl-1,5,7-triazabicyclo[4.4.0]dec-5-ene (MTBD) as catalysts revealed no activity in the studied reaction.
Dihydropyridines, carbamoylmethyl esters, Carboxylic Acids, Organic chemistry, Esters, aminolysis, Article, Catalysis, cyclic amines, QD241-441, secondary amines, 1,4-dihydropyridines; ethoxycarbonylmethyl esters; aminolysis; carbamoylmethyl esters; secondary amines; cyclic amines; 1,5,7-triazabicyclo[4.4.0]dec-5-ene, 1,5,7-triazabicyclo[4.4.0]dec-5-ene, Solvents, Amines, ethoxycarbonylmethyl esters, 1,4-dihydropyridines
Dihydropyridines, carbamoylmethyl esters, Carboxylic Acids, Organic chemistry, Esters, aminolysis, Article, Catalysis, cyclic amines, QD241-441, secondary amines, 1,4-dihydropyridines; ethoxycarbonylmethyl esters; aminolysis; carbamoylmethyl esters; secondary amines; cyclic amines; 1,5,7-triazabicyclo[4.4.0]dec-5-ene, 1,5,7-triazabicyclo[4.4.0]dec-5-ene, Solvents, Amines, ethoxycarbonylmethyl esters, 1,4-dihydropyridines
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