2-trifluoromethylquinolines 5 are synthesized in high yields using a perfluoroalkylated gem-iodoacetoxy derivative 3 and arylamines 4. The intermediate of this reaction, 2-trifluoromethyl-1,5-diazapentadiene compound 6, was isolated. The procedures are easy, and yields are in general high. This sequence represents a valuable new synthesis of substituted 2-trifluoromethylquinolines and of 2-trifluoromethyl-diazapentadienes (vinamidine compounds).
Substituted 3-phenoxy-3-perfluoroalkylprop-2-enals 3a-s are synthesized in high yields starting from a gem-iodoacetoxy derivative 1 and phenoxides 2. Then efficient syntheses of push-pull derivatives 4, 5,8a,b, and nonconjugated analogues 6 and 7 illustrate the synthetic potentialities of 3. Stereochemical studies of these perfluoroalkyl-containing trisubstituted olefinic derivatives 3-8b revealed that the (4)J(CF) coupling constant observed in the (13)C NMR spectra was crucial in the determination of their configurations and conformations in solution. The solvent polarity effect on the stereochemistry of push-pull compounds 3-5 and 8a,b was studied. Unusual significant medium polarity effect on the stereochemistry of imino enol ether derivative 4 was observed.
The synthesis of substituted 2-(trifluoromethyl)- and 2-(perfluoroalkyl)-2-hydroxy-2H-chromenes 2a-o was achieved in good yields by intramolecular cyclization of 3-(perfluoroalkyl)-3-phenoxypropenals 1 in the presence of aluminum chloride. Then a Lewis acid mediated nucleophilic reaction with silyl enol ethers 3 proceeded with complete regiospecificity to afford 4-functional 2-(trifluoromethyl)- and 2-(perfluoroalkyl)-4H-chromenes 4a-p with high yields.
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