Retro-Mannich reactions of 3-alkyl-3,4-dihydro-2H-1,3-benz[e]oxazines and the synthesis of axially chiral resorcinarenes |
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Authors: | Philip CBulman PageHarry Heaney Matthew J McGrathEdward P Sampler Robert F Wilkins |
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Institution: | Department of Chemistry, Loughborough University, Loughborough, Leicestershire LE11 3TU, UK |
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Abstract: | Intermediates involved in the conversion of 3-alkyl-3,4-dihydro-2H-1,3-benze]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. |
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Keywords: | heterocycles aminol ethers o-quinone methides axially chiral resorcinarenes |
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