Haloacetylated Enol Ethers, 19: [1] Synthesis of 3-(2-Thienyl)- and 3-(2-Furyl)-5-trihalomethyl Substituted Azoles

Abstract

Heterocyclization of 1,1,1-trifluoro[chloro]-4-methoxy-4-[2-tienyl]-3-buten-2-one and 1,1,1-trifluoro[chloro]-4-methoxy-4-[2-furyl]-3-buten-2-ones into isoxazoles and pyrazoles derivatives as a new type of trihalomethylated bicyclic heterocycles is reported.

[3+2] cyclocondensation - furyl isoxazoles - thienyl isoxazoles - furyl pyrazoles - thienyl pyrazoles

References

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¹⁹F NMR in CDCl₃ from external CFCl₃ (δ = 0.0 ppm): for 5-trifluoromethyl-4,5-dihydroisoxazoles and 5-trifluoromethyl-1-phenyl-4,5-dihydropyrazoles the δ were in range -78.1 to -82.9 ppm; for 5-trifluoromethylisoxazoles δ = -64.1 to -64.5 ppm; for 5-trifluoromethyl-1H-pyrazoles δ = -62.8 to -63.5 ppm; from a mixture of isomers ( [1,3] 15a′ and [1,5] 15a) were obtained two signals at -62.8 and -64.1 ppm with the same intensity.

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