Synthesis of xanthones, thioxanthones, and acridones by the coupling of arynes and substituted benzoates.
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.
Zhao
Jian
J
Department of Chemistry, Iowa State University, Ames, Iowa 50011, USA.
Larock
Richard C
RC
D000166:Acridines / Q000138:chemical synthesis* / Q000737:chemistry; D001565:Benzoates / Q000737:chemistry*; D003500:Cyclization; D006841:Hydrocarbons, Aromatic / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism; D013438:Sulfhydryl Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013892:Thioxanthenes / Q000138:chemical synthesis / Q000737:chemistry; D044004:Xanthones / Q000138:chemical synthesis* / Q000737:chemistry
D000166:Acridines; D001565:Benzoates; D006841:Hydrocarbons, Aromatic; D013438:Sulfhydryl Compounds; D013892:Thioxanthenes; D044004:Xanthones; C484911:thioxanthone