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

Literature Information

Publication Date 2018-08-15
DOI 10.1039/C8OB01684D
Impact Factor 3.876
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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.

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Organic & Biomolecular Chemistry

Organic & Biomolecular Chemistry
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Organic & Biomolecular Chemistry (OBC) publishes original and high impact research and reviews in organic chemistry. We welcome research that shows new or significantly improved protocols or methodologies in total synthesis, synthetic methodology or physical and theoretical organic chemistry as well as research that shows a significant advance in the organic chemistry or molecular design aspects of chemical biology, catalysis, supramolecular and macromolecular chemistry, theoretical chemistry, mechanism-oriented physical organic chemistry, medicinal chemistry or natural products. Articles published in the journal should report new work which makes a highly-significant impact in the field. Routine and incremental work is generally not suitable for publication in the journal. More details about key areas of our scope are below. In all cases authors should include in their article clear rationale for why their research has been carried out.

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