Trifluoromethylated 4,5-Dihydro-1,2,4-triazin-6(1H)-ones via (3+3)-Annulation of Nitrile Imines with α-Amino Esters
| Autor: | Anna Kowalczyk, Kamil Świątek, Małgorzata Celeda, Greta Utecht-Jarzyńska, Agata Jaskulska, Katarzyna Gach-Janczak, Marcin Jasiński |
|---|---|
| Jazyk: | angličtina |
| Rok vydání: | 2023 |
| Předmět: |
triazinones
nitrile imines amino acids (3+3)-annulation fluorinated heterocycles anticancer activity Technology Electrical engineering. Electronics. Nuclear engineering TK1-9971 Engineering (General). Civil engineering (General) TA1-2040 Microscopy QH201-278.5 Descriptive and experimental mechanics QC120-168.85 |
| Zdroj: | Materials, Vol 16, Iss 2, p 856 (2023) |
| Druh dokumentu: | article |
| ISSN: | 1996-1944 |
| DOI: | 10.3390/ma16020856 |
| Popis: | The synthesis of two series of monocyclic and bicyclic trifluoromethylated 4,5-dihydro-1,2,4-triazin-6(1H)-one derivatives based on (3+3)-annulation of methyl esters derived from natural α-amino acids with in situ generated trifluoroacetonitrile imines has been described. The devised protocol is characterized by a wide scope, easily accessible substrates, remarkable functional group tolerance, and high chemical yield. In reactions with chiral starting materials, no racemization at the stereogenic centers was observed and the respective enantiomerically pure products were obtained. Selected functional group interconversions carried out under catalytic hydrogenation and mild PTC oxidation conditions were also demonstrated. |
| Databáze: | Directory of Open Access Journals |
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