Direct Aminolysis of Ethoxycarbonylmethyl 1,4-Dihydropyridine-3-carboxylates
AbstractThe 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. View Full-Text
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Vigante, B.; Rucins, M.; Plotniece, A.; Pajuste, K.; Luntena, I.; Cekavicus, B.; Bisenieks, E.; Smits, R.; Duburs, G.; Sobolev, A. Direct Aminolysis of Ethoxycarbonylmethyl 1,4-Dihydropyridine-3-carboxylates. Molecules 2015, 20, 20341-20354.
Vigante B, Rucins M, Plotniece A, Pajuste K, Luntena I, Cekavicus B, Bisenieks E, Smits R, Duburs G, Sobolev A. Direct Aminolysis of Ethoxycarbonylmethyl 1,4-Dihydropyridine-3-carboxylates. Molecules. 2015; 20(11):20341-20354.Chicago/Turabian Style
Vigante, Brigita; Rucins, Martins; Plotniece, Aiva; Pajuste, Karlis; Luntena, Iveta; Cekavicus, Brigita; Bisenieks, Egils; Smits, Rufus; Duburs, Gunars; Sobolev, Arkadij. 2015. "Direct Aminolysis of Ethoxycarbonylmethyl 1,4-Dihydropyridine-3-carboxylates." Molecules 20, no. 11: 20341-20354.