Abstract
An improved procedure to prepare a series of five 5-alkoxy-1,1,1,2,2-pentafluoro-4-alken-3-ones (CF3CF2C(O)C(R 2 )=C(R 1 )OR, where R 2 /R = H/Et, H/Me, Me/Et, -(CH2)2- , -(CH2)3-, and R 1 = H, Me) in good yields (71 - 82%) and in an up to molar scale from the acylation reaction of enol ethers with pentafluoropropionic anhydride is described. These compounds were cyclocondensed with different dinucleophiles, such as hydroxylamine, 1,2-dimethylhydrazine and phenylhydrazine, to obtain a series of pentafluoroethyl substituted 4,5-dihydroisoxazoles, pyrazolium chlorides and pyrazoles, respectively, in one-pot procedures with moderate to very good yields (60 - 95%).
Highlights
Heterocycles containing perfluoroalkyl groups are very attractive compounds due to their biological properties.[1]
Pyrazolium salts have been used as coloring pigments5a-c and as reagents in organic synthesis.5d
CF3, CCl3 and CHCl2],7,8 which are important halogen-containing building blocks, in heterocyclic preparations,[9] e.g., isoxazoles, pyrazoles, pyrazolium chlorides, pyrrolidinones, pyrimidines and pyridinones, pyridines, thiazines, diazepines and thiazolo pyrimidinones, has been extensively described by our research group, there is a lack of literature on the use of 4-alkoxy-3-alken-2
Summary
Heterocycles containing perfluoroalkyl groups are very attractive compounds due to their biological properties.[1]. CF3, CCl3 and CHCl2],7,8 which are important halogen-containing building blocks, in heterocyclic preparations,[9] e.g., isoxazoles, pyrazoles, pyrazolium chlorides, pyrrolidinones, pyrimidines and pyridinones, pyridines, thiazines, diazepines and thiazolo pyrimidinones, has been extensively described by our research group, there is a lack of literature on the use of 4-alkoxy-3-alken-2-
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