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- Title
Efficient Synthesis of (1,2,3-Triazol-1-yl)methylpyrimidines from 5-Bromo-1,1,1-trifluoro-4-methoxypent-3-en-2-one.
- Authors
Aquino, Estefania da C.; Lobo, Marcio M.; Leonel, Guilherme; Martins, Marcos A. P.; Bonacorso, Helio G.; Zanatta, Nilo
- Abstract
5-Bromo-1,1,1-trifluoro-4-methoxypent-3-en-2-one was used as an efficient precursor for the synthesis of a new series of (1,2,3-triazol-1-yl)methyl-pyrimidine biheterocycles. For this stepwise synthesis, the 5-bromo-1,1,1-trifluoro-4-methoxypent-3-en-2-one was first converted into 5-azido-1,1,1-trifluoro-4-methoxypent-3-en-2-one through a nucleophilic substitution of the bromine by an azide group. This was then followed by an azide-alkyne cycloaddition reaction (click chemistry) to give the key intermediate 5-[4-alkyl(aryl)-1H-1,2,3-triazol-1-yl]-1,1,1-trifluoro-4-methoxypent-3-en-2-ones. These were cyclocondensed with 2-methylisothiourea sulfate to give a series of 2-(methylthio)-4-(1,2,3-triazol-1-yl)methyl-6-(trifluoromethyl)pyrimidines. Additionally, the 2-methylthiopyrimidine products were used to prepare a new series of 2-amino-4-(1,2,3-triazol-1-yl)methyl-6-(trifluoromethyl)pyrimidines.
- Subjects
NUCLEOPHILIC substitution reactions; PYRIMIDINE synthesis; RING formation (Chemistry); BROMINE; AMINES; CARBON compounds spectra
- Publication
European Journal of Organic Chemistry, 2017, Vol 2017, Issue 2, p306
- ISSN
1434-193X
- Publication type
Article
- DOI
10.1002/ejoc.201601234