Direct Aminolysis of Ethoxycarbonylmethyl 1,4-Dihydropyridine-3-carboxylates.
In: Molecules, Jg. 20 (2015-11-01), Heft 11, S. 20341-20354
Online
academicJournal
Zugriff:
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. [ABSTRACT FROM AUTHOR]
Titel: |
Direct Aminolysis of Ethoxycarbonylmethyl 1,4-Dihydropyridine-3-carboxylates.
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Autor/in / Beteiligte Person: | Vigante, Brigita ; Rucins, Martins ; Plotniece, Aiva ; Pajuste, Karlis ; Luntena, Iveta ; Cekavicus, Brigita ; Bisenieks, Egils ; Smits, Rufus ; Duburs, Gunars ; Sobolev, Arkadij |
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Zeitschrift: | Molecules, Jg. 20 (2015-11-01), Heft 11, S. 20341-20354 |
Veröffentlichung: | 2015 |
Medientyp: | academicJournal |
ISSN: | 1420-3049 (print) |
DOI: | 10.3390/molecules201119697 |
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