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15.4.5.4.3.1.1.1 Amination

DOI: 10.1055/sos-SD-115-01218

Silva, V. L. M.; Pinto, D. C. G. A.; Santos, C. M. M.; Rocha, D. H. A.Science of Synthesis Knowledge Updates, (20223417.

The most recent approaches for the amination of quinolines involve metal-catalyst- and ligand-free conditions and do not require preactivated substrates or high temperatures. Thus, several quinolines undergo oxidative radical amination with saccharin in the presence of [bis(trifluoroacetoxy)iodo]benzene [PhI(OCOCF3)2] using ethyl acetate as solvent to give the corresponding quinolin-2-amines in high yields.[‌545‌] Alternatively, Selectfluor [1-(chloromethyl)-4-fluoro-1,4-diazoniabicyclo-[2.2.2]octane bis(tetrafluoroborate)], an important electrophilic fluorinating agent, promotes regioselective nucleophilic functionalization of quinolines 501 with 1H-benzo[d][1,2,3]triazoles 502 in acetonitrile at room temperature to provide 2-(1H-benzo[d][1,2,3]triazol-1-yl)quinolines 503 in up to 96% yield (Scheme 183). This strategy has been extended to other nitrogen-containing heterocycles such as pyrazoles, triazoles, and 1H-tetrazoles 504, providing products 505 (Table 1).[‌546‌]

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