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Synlett 1997; 1997(7): 839-841
DOI: 10.1055/s-1997-5743
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Anionic Homologous Fries Rearrangement of O-(2-Methylaryl)carbamates. A Regiospecific Route to Benzo[b]furan-2(3H)-ones including an Unnamed Metabolite from Helenium Species

A. V. Kalinin1 , M. A. J. Miah1 , S. Chattopadhyay1 , M. Tsukazaki1 , M. Wicki1 , T. Nguen1 , A. L. Coelho1 , M. Kerr2 , V. Snieckus3
  • 1Guelph-Waterloo Centre for Graduate Work in Chemistry, University of Waterloo, Waterloo, Ontario, Canada, N2L 3G1
  • 2Department of Chemistry, Acadia University, Wolfville, New Brunswick, Canada, BOP 1XO, Fax 902 5421454; e-mail mkerr@ace.acadiau.ca
  • 3Guelph-Waterloo Centre for Graduate Work in Chemistry, University of Waterloo, Waterloo, Ontario, Canada, N2L 3G1, Fax 519 7465884; e-mail snieckus@buli.UWaterloo.ca
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Publication History

Publication Date:
31 December 2000 (online)

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A new LDA mediated O → C carbamoyl migration, 3 provides a general and efficient route to aryl acetamides 5, precursors to the benzo- and naphthofuranones 7, one of which serves as a starting material for a short synthesis of naturally-occurring benzofuranolactol 11 isolated from several Helenium species.

anionic homologous Fries rearrangement - O-arylcarbamates - benzo[b]furan-2-(3H)-ones