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Synlett 1998; 1998(10): 1141-1143
DOI: 10.1055/s-1998-1878
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The First High-yielding Benzyne Cyclisation Using a Phenolic Nucleophile: A New Route to Xanthenes

David W. Knight* , Paul B. Little
  • *Chemistry Department, Cardiff University, P.O. Box 912, Cardiff, CF1 3TB, UK; Fax UK(0)12 22 87 42 10; E-mail: knightdw@cf.ac.uk
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Publication History

Publication Date:
31 December 2000 (online)

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Condensation of dianion 2 derived from aminobenzotriazole 1 with O-benzyl-salicylaldehydes 11 gives intermediate alcohols 12 in good yields. Double hydrogenolysis gives phenols 13 which, upon deprotection and benzyne generation using N-iodosuccinimide, undergo smooth cyclisation to give the iodo-xanthenes 14 in excellent overall yields.

benzyne - intramolecular - nucleophilic - trapping - xanthene

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