Journal
MOLECULES
Volume 26, Issue 15, Pages -Publisher
MDPI
DOI: 10.3390/molecules26154415
Keywords
beta-diketones; 4-pyrones; fluorinated heterocycles; regioselective bromination
Funding
- Russian Science Foundation [18-13-00186]
- Russian Science Foundation [18-13-00186] Funding Source: Russian Science Foundation
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A convenient and general method for the direct synthesis of 2-aryl-6-(trifluoromethyl)-4-pyrones and 2-aryl-5-bromo-6-(trifluoromethyl)-4-pyrones has been developed through a one-pot oxidative cyclization approach. This strategy has broad application potential for the preparation of pyrones and their derivatives. The prepared pyrones can be used for the synthesis of biologically important azaheterocycles containing CF3 group.
A convenient and general method for the direct synthesis of 2-aryl-6-(trifluoromethyl)-4-pyrones and 2-aryl-5-bromo-6-(trifluoromethyl)-4-pyrones has been developed on the basis of one-pot oxidative cyclization of (E)-6-aryl-1,1,1-trifluorohex-5-ene-2,4-diones via a bromination/dehydrobromination approach. This strategy was also applied for the preparation of 2-phenyl-6-polyfluoroalkyl-4-pyrones and their 5-bromo derivatives. Conditions of chemoselective enediones bromination were found and the key intermediates of the cyclization of bromo-derivatives to 4-pyrones were characterized. Synthetic application of the prepared 4-pyrones has been demonstrated for the construction of biologically important CF3-bearing azaheterocycles, such as pyrazoles, pyridones, and triazoles.
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