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Synfacts 2010(6): 0633-0633  
DOI: 10.1055/s-0029-1219876
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart ˙ New York

Radical-Mediated Decarboxylative Route to Naphtho[2,3-a]carbazoles

Contributor(s): Victor Snieckus, Toni Rantanen
C. Ding, S. Tu, Q. Yao*, F. Li, Y. Wang, W. Hu*, A. Zhang*
Shanghai Institute of Materia Medica, China Pharmaceutical University, Nanjing and Capital Normal University, Beijing, P. R. of China
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Publication History

Publication Date:
20 May 2010 (online)

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Significance

Reported is a strategy for the one-pot construction of pentacyclic carbazoles from the reaction of bromo-1,4-naphthoquinones with indol-3-ylpropanoic acid catalyzed by silver acetate and utilizing ammonium persulfate as oxidant. These conditions are based on those used for the synthesis of benzo[a]anthraquinones from 1,4-naphthoquinones and aryl propanoic acids (C. Y. Ding et al. J. Org. Chem. 2009, 74, 6111) in three separate steps and proceeds by a fairly complex pathway involving decarboxylative radical alkylation, cyclization, and aromatization under oxidative conditions. Regioselective radical coupling is observed for X = Br but, surprisingly, not for X = H. For X = OH or OAc, the reaction did not proceed at all.