The 2-amino-1,4-naphthoquinones and 2-amino-3-indolylnaphthoquinones by the t-BuOK mediated oxidative coupling amination has been developed. The 2-amino-3-indolylnaphthoquinones were conducted further transformation to polycyclic N-heterocycles.
Concise one-pot biarylamination of quinones with arylamines was developed to synthesize N-arylamine-functionalized p-iminoquinones derivatives. The approach employed AgOAc as the catalyst and (NH4)2S2O8 as the oxidant in the presence of 3-chlorophenylboronic acid, giving a series of N-arylamine-functionalized p-iminoquinone derivatives in moderate to good yields whereas reaction in the absence of the 3-chlorophenylboronic acid, gave a series of N-arylamine-functionalized 1,4-naphthoquinone derivatives. This catalytic approach represents a step-economic and convenient strategy for the difunctionalization of quinones.
An atom-economical and environmentally benign approach for the synthesis of 3-indolylquinones was achieved successfully via direct oxidative C–C coupling of quinones/hydroquinones with indoles using (NH4)2S2O8 in dichloroethane at 80 °C. The efficiency of this catalytic approach was established by a broad scope of substrates involving quinones and hydroquinones to give high yields (61–93%) of 3-indolylquinones. The present protocol is simple, practical, and show good functional group tolerance. In addition, the obtained 3-indolylnaphthoquinones were conducted to further transformation to synthesize 2-amino-3-indolylnaphthoquinone and polycyclic N-heterocycles, respectively.
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