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The synthetic routes to the desired compounds are illustrated in Scheme 1. The intermediates1, 7 2, 7 4, 8 5 9and6 10 were prepared according to the methods in the literatures. The key intermediate, 3, was prepared from 2by lithiation withn-butyllithium and boronation with trimethyl borate (55% yield). However, we could not obtain compound 3by Grignard reaction because compound2did not react with magnesium (Mg) and failed to produce a Grignard reagent. The target compounds,1B-TPA,
2B-TPA and 3B-TPA, were synthesized by Suzuki coupling reactions of 3with the corresponding halogenated triphenyl-amines4, 5and6in the presence of a palladium(0) catalyst (36– 53% yield). The products exhibited good solubility in common organic solvents and were purified by silica gel column chro-matography using dichloromethane–n-hexane as eluent. Their chemical structures were confirmed with proton nuclear magnetic resonance (1 H-NMR), high resolution massspectrometer (HRMS), Fourier transform infrared spectroscopy (FT-IR) and elementary analysis (EA). |
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