Direct Aminolysis of Ethoxycarbonylmethyl 1,4-Dihydropyridine-3-carboxylates
| Autor: | Martins Rucins, Brigita Cekavicus, Egils Bisenieks, Gunars Duburs, Aiva Plotniece, Rufus Smits, Arkadij Sobolev, Brigita Vigante, Karlis Pajuste, Iveta Luntena |
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| Rok vydání: | 2015 |
| Předmět: |
Dihydropyridines
carbamoylmethyl esters Carboxylic Acids Pharmaceutical Science Conjugated system Medicinal chemistry Catalysis Article Analytical Chemistry lcsh:QD241-441 chemistry.chemical_compound Aminolysis lcsh:Organic chemistry secondary amines 1 4-dihydropyridines ethoxycarbonylmethyl esters aminolysis cyclic amines 1 5 7-triazabicyclo[4.4.0]dec-5-ene Drug Discovery Pyridine Organic chemistry Imidazole Physical and Theoretical Chemistry Amines Guanidine Triethylamine Alkyl chemistry.chemical_classification Organic Chemistry Esters chemistry Chemistry (miscellaneous) Solvents Molecular Medicine |
| Zdroj: | Molecules Volume 20 Issue 11 Pages 20341-20354 Molecules, Vol 20, Iss 11, Pp 20341-20354 (2015) Molecules; Volume 20; Issue 11; Pages: 20341-20354 |
| ISSN: | 1420-3049 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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