A novel CAN??SiO2??mediated one??pot oxidation of 1??keto??1, 2, 3, 4??tetrahydrocarbazoles to carbazoloquinones: Efficient syntheses of murrayaquinone A and …

S Chakraborty, G Chattopadhyay…

Index: Chakraborty, Suchandra; Chattopadhyay, Gautam; Saha, Chandan Journal of Heterocyclic Chemistry, 2011 , vol. 48, # 2 p. 331 - 338

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Citation Number: 14

Abstract

Abstract 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-SiO 2-mediated 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- ...