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Issue 40, 2018
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Syntheses of 12H-benzo[a]xanthen-12-ones and benzo[a]acridin-12(7H)-ones through Au(I)-catalyzed Michael addition/6-endo-trig cyclization/aromatization cascade annulation

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Abstract

A multifaceted gold(I)-catalyzed aromaticity-driven double 6-endo cascade cyclization strategy to synthesize both 12H-benzo[a]xanthen-12-ones and benzo[a]acridin-12(7H)-ones, whose core motifs xanthone and acridone both exist as important scaffolds in an immense number of bioactive compounds, was developed. The scopes of this strategy were examined by using a batch of synthetic 1,3-diphenylprop-2-yn-1-one substrates. To probe the mechanism of this cyclization a control experiment for synthesizing intermediates was performed. Thus, a putative mechanism was determined according to this experiment and previous studies.

Graphical abstract: Syntheses of 12H-benzo[a]xanthen-12-ones and benzo[a]acridin-12(7H)-ones through Au(i)-catalyzed Michael addition/6-endo-trig cyclization/aromatization cascade annulation

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Publication details

The article was received on 15 Jul 2018, accepted on 14 Aug 2018 and first published on 15 Aug 2018


Article type: Paper
DOI: 10.1039/C8OB01684D
Citation: Org. Biomol. Chem., 2018,16, 7361-7374

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    Syntheses of 12H-benzo[a]xanthen-12-ones and benzo[a]acridin-12(7H)-ones through Au(I)-catalyzed Michael addition/6-endo-trig cyclization/aromatization cascade annulation

    Z. Xiong, X. Zhang, Y. Li, X. Peng, J. Fu, J. Guo, F. Xie, C. Jiang, B. Lin, Y. Liu and M. Cheng, Org. Biomol. Chem., 2018, 16, 7361
    DOI: 10.1039/C8OB01684D

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