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Synthesis of xanthones, thioxanthones, and acridones by the coupling of arynes and substituted benzoates.

ABSTRACT: The reaction of silylaryl triflates, CsF, and ortho-heteroatom-substituted benzoates affords a general and efficient way to prepare biologically interesting xanthones, thioxanthones, and acridones. This chemistry presumably proceeds by a tandem intermolecular nucleophilic coupling of the benzoate with an aryne and a subsequent intramolecular electrophilic cyclization.

SUBMITTER: Zhao J

PROVIDER: S-EPMC2529457 | biostudies-literature | 2007 Jan

REPOSITORIES: biostudies-literature

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Synthesis of xanthones, thioxanthones, and acridones by the coupling of arynes and substituted benzoates.

Zhao Jian J Larock Richard C RC

The Journal of organic chemistry 20070101 2

The reaction of silylaryl triflates, CsF, and ortho-heteroatom-substituted benzoates affords a general and efficient way to prepare biologically interesting xanthones, thioxanthones, and acridones. This chemistry presumably proceeds by a tandem intermolecular nucleophilic coupling of the benzoate with an aryne and a subsequent intramolecular electrophilic cyclization. ...[more]

PMID: 17221977

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