Synthesis of highly-functionalised pyridines via hetero-Diels-Alder methodology: reaction of 3-siloxy-1-aza-1,3-butadienes with electron deficient acetylenes |
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Authors: | Matthew D. Fletcher Timothy E. Hurst Timothy J. Miles |
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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 |
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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. |
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Keywords: | Hetero-Diels-Alder reaction Pyridines Microwave irradiation |
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