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Keywords = ethoxycarbonylmethyl esters

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14 pages, 1839 KB  
Article
Direct Aminolysis of Ethoxycarbonylmethyl 1,4-Dihydropyridine-3-carboxylates
by Brigita Vigante, Martins Rucins, Aiva Plotniece, Karlis Pajuste, Iveta Luntena, Brigita Cekavicus, Egils Bisenieks, Rufus Smits, Gunars Duburs and Arkadij Sobolev
Molecules 2015, 20(11), 20341-20354; https://doi.org/10.3390/molecules201119697 - 12 Nov 2015
Cited by 8 | Viewed by 9559
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 [...] Read more.
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. Full article
(This article belongs to the Collection Heterocyclic Compounds)
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3 pages, 123 KB  
Short Note
Synthesis of ({8-[4,6-Bis-(bis-pyridin-2-ylmethyl-amino)-[1,3,5]triazine-2-ylamino]-octyl}—ethoxycarbonylmethyl-amino)-acetic acid ethyl ester
by Daniel Vomasta and Burkhard König
Molbank 2007, 2007(4), M557; https://doi.org/10.3390/M557 - 7 Sep 2007
Viewed by 4062
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