A Novel CAN-SiO2-Mediated One-Pot Oxidation of 1-Keto-1,2,3,4-tetrahydrocarbazoles to Carbazoloquinones: Efficient Syntheses of Murrayaquinone A and Koeniginequinone A

[摘要]：One-pot oxidations of substituted 1-keto-1,2,3,4-tetrahydrocarbazoles (1) to carbazole-1,4-quinones (2) are efficiently carried out by CAN-SiO2-mediatect reaction. This generalized protocol was successfully extended to the synthesis of two naturally occurring carbazoloquinones: murrayaquinone A (2b) and koeniginequinone A (2g). A plausible mechanism for this novel reaction involves formation of a 9-hydroxy-2,3,4,9-tetrahydro-1H-carbazole-1-one followed by rearrangement to 1-hydroxycarbazole derivatives, which are further oxidized by cerium (IV) to carbazoloquinones.

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