The reaction of 2-(1-hydropolyfluoro-1-alkenyl)-4H-3,1-benzoxin-4-ones with dinucleophilic reagents: a convenient route to fluoroalkylated nitrogen-containing tricyclic compounds |
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Authors: | Xian-Jin Yang He-Jun Lu |
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Institution: | Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032, People's Republic of China |
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Abstract: | The reactions of 2-(1-hydropolyfluoro-1-alkenyl)-4H-3,1-benzoxin-4-ones (2) with hydrazine hydrate and phenyl hydrazine were investigated. The reaction of 2 with hydrazine hydrate in ethanol under reflux condition readily gave 2-fluoroalkyl-4H-pyrazolo5,1-b]quinazolin-9-ones (3) in high yields. The reaction of 2 with phenyl hydrazine, however, resulted in the formation of 2-(2-phenyl-5-fluoroalkyl-2H-pyrazol-3-yl) benzoic acids (7). Further treatment of 7 with PPA gave 1-phenyl-4,9-dihydro-3-fluoroalkyl-1H-pyrozolo3,4-b]quinolin-4-ones (4) in 65-80% overall yields. |
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Keywords: | 2-(1-Hydropolyfluoro-1-alkenyl)-4H-3 1-benzoxin-4-ones Hydrazine hydrate 2-Fluoroalkyl-4H-pyrazolo[5 1-b]quinazolin-9-ones 3-Fluoroalkyl-1H-pyrozolo[3 4-b]quinolin-4-ones Phenyl hydrazine |
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