Thermally-induced skeletal rearrangement of (Z)-O-propargylic α,β-unsaturated aldoximes to multisubstituted pyridine oxides |
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| Authors: | Itaru Nakamura Dong ZhangMasahiro Terada |
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| Institution: | a Research and Analytical Center for Giant Molecules, Graduate School of Science, Tohoku University, Sendai 980-8578, Japan
b Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980-8578, Japan |
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| Abstract: | (Z)-Propargylic oxime ethers derived from α,β-unsaturated aldehydes were converted to the corresponding 2,3,6-trisubstituted pyridine oxides in moderate to acceptable yields with high regioselectivity. The reaction proceeds via a tandem thermal 2,3] rearrangement, 4π electrocyclization, and ring expansion. |
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| Keywords: | Pyridine Oxime Skeletal rearrangement Alkyne Electrocyclization |
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