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Synthesis of highly-functionalised pyridines via hetero-Diels-Alder methodology: reaction of 3-siloxy-1-aza-1,3-butadienes with electron deficient acetylenes
Authors:Matthew D. Fletcher  Timothy E. Hurst  Timothy J. Miles
Affiliation:a Department of Chemistry, University of Wales Bangor, Bangor, Gwynedd LL57 2UW, UK
b Department of Chemistry, University of Exeter, Stocker Road, Exeter EX4 4QD, UK
c School of Chemistry, University of Nottingham, University Park, Nottingham NG7 2RD, UK
d GlaxoSmithKline, New Frontiers Science Park, Third Avenue, Harlow, Essex CM19 5AW, UK
Abstract:
The hetero-Diels-Alder reaction between 1-aza-3-siloxy-1,3-butadienes and electron deficient acetylenes is described. The reactivity of a range of α,β-unsaturated oximes and hydrazones is assessed in the synthesis of tri- and tetra-substituted pyridines bearing an oxygen functionality at C-3. Microwave irradiation has been employed to decrease the extended reaction times and increase the poor yields often associated with this reaction.
Keywords:Hetero-Diels-Alder reaction   Pyridines   Microwave irradiation
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