Retro-Mannich reactions of 3-alkyl-3,4-dihydro-2H-1,3-benz e oxazines and the synthesis of axially chiral resorcinarenes

Philip C. Bulman Page, Harry Heaney, Matthew J. McGrath, Edward P. Sampler, Robert F. Wilkins

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Abstract

Intermediates involved in the conversion of 3-alkyl-3,4-dihydro-2H-1,3-benz[e]oxazines into 2-N,N-dialkylaminomethylphenol derivatives, using morpholine and other high boiling secondary amines, have been identified and characterised. Additional experiments have established the involvement of o-quinone methide intermediates in the retro-Mannich reactions. Axially chiral resorcinarenes have been prepared by utilising the exchange reactions. (C) 2003 Elsevier Science Ltd. All rights reserved.
Original languageEnglish
Pages (from-to)2965-2970
Number of pages6
JournalTetrahedron Letters
Volume44
Issue number14
DOIs
Publication statusPublished - 31 Mar 2003

Keywords

  • SOLVENT
  • resorcinarenes
  • GENERATION
  • DERIVATIVES
  • O-QUINONE METHIDE
  • axially chiral
  • heterocycles
  • o-quinone methides
  • REACTIVITY
  • aminol ethers

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