Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2020, Issue 34, Pages 5527-5536Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.202000879
Keywords
beta-Enamino diketones; Pyrimidines; Pyrimidin-4(3H)-ones; Trifluoromethyl
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Funding
- (FundacAo de Amparo a Pesquisa do Estado do Rio Grande do Sul - FAPERGS) - FAPERGS/CNPq - PRONEX [16/2551-0000477-3]
- CNPq [407898/2018-2]
- CAPES
- CNPq
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A regio- and chemoselective method for the preparation of 6-trifluoromethyl-5-benzoyl-2-methylsulfanyl pyrimidines and their pyrimidin-4(3H)-one analogues, from the cyclocondensation reaction of trifluoromethyl beta-enamino diketones with non-symmetric 2-methylisothiourea sulfates is reported. These diketones functioned as dual substrates by providing both products with high regioselectivity (onlyN(3)-substituted isomer was observed) and high chemoselectivity. A new feature provided by the starting material proposed herein is the possibility to either maintain or eliminate the trifluoromethyl group, by choosing the solvent.
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