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Synlett 1997; 1997(9): 1079-1080
DOI: 10.1055/s-1997-1532
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Intramolecular Anionic Friedel-Crafts Equivalents. An Expeditious Synthesis of 4H-1,2-Benzothiazin-4-one 1,1-Dioxides from N-Arylsulfonylated Amino Acids

Wouter I. Iwema Bakker, O. B. Familoni, James Padfield, Victor Snieckus*
  • *Guelph-Waterloo Centre for Graduate Work in Chemistry, University of Waterloo, Waterloo, Ontario, Canada, N2L 3G1, Fax: 519-746-5884; email: snieckus@buli.uwaterloo.ca
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Publication Date:
31 December 2000 (online)

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Treatment of compounds 1, readily available from amino acids, with excess LDA furnishes benzothiazinones 2 in modest to good yields (Table); variations of carbanion-mediated reactions led to benzothiazepinones (Table, entries 12 and 13) and dibenzothiazepinone (5).

directed ortho metalation - benzothiazinones - benzothiazepinones - N-arylsulfonylated amino acids