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Molecules 2015, 20(11), 20341-20354; doi:10.3390/molecules201119697

Direct Aminolysis of Ethoxycarbonylmethyl 1,4-Dihydropyridine-3-carboxylates

Latvian Institute of Organic Synthesis, Aizkraukles str. 21, Riga LV-1006, Latvia
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Academic Editor: Philippe Belmont
Received: 24 September 2015 / Revised: 22 October 2015 / Accepted: 27 October 2015 / Published: 12 November 2015
(This article belongs to the Collection Heterocyclic Compounds)
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Abstract

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. View Full-Text
Keywords: 1,4-dihydropyridines; ethoxycarbonylmethyl esters; aminolysis; carbamoylmethyl esters; secondary amines; cyclic amines; 1,5,7-triazabicyclo[4.4.0]dec-5-ene 1,4-dihydropyridines; ethoxycarbonylmethyl esters; aminolysis; carbamoylmethyl esters; secondary amines; cyclic amines; 1,5,7-triazabicyclo[4.4.0]dec-5-ene
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

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.

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