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Trifluoromethylated 4,5-Dihydro-1,2,4-triazin-6(1H)-ones via (3+3)-Annulation of Nitrile Imines with α-Amino Esters.

ABSTRACT: 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.

SUBMITTER: Kowalczyk A

PROVIDER: S-EPMC9864844 | biostudies-literature | 2023 Jan

REPOSITORIES: biostudies-literature

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Trifluoromethylated 4,5-Dihydro-1,2,4-triazin-6(1<i>H</i>)-ones via (3+3)-Annulation of Nitrile Imines with α-Amino Esters.

Kowalczyk Anna A Świątek Kamil K Celeda Małgorzata M Utecht-Jarzyńska Greta G Jaskulska Agata A Gach-Janczak Katarzyna K Jasiński Marcin M

Materials (Basel, Switzerland) 20230116 2

The synthesis of two series of monocyclic and bicyclic trifluoromethylated 4,5-dihydro-1,2,4-triazin-6(1<i>H</i>)-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 ste ...[more]

PMID: 36676595

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