期刊
TETRAHEDRON LETTERS
卷 50, 期 4, 页码 448-451出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2008.11.033
关键词
1-Azadienes; Azomethine ylide; Coumarins; 1,3-Dipolar cycloadditions; Hetero-Diels-Alder reactions; Pyridocoumarins
资金
- State Scholarships Foundation (IKY), Greece
O-Methyl-4-coumarincarbaldehyde oxime reacted as an azadiene with electron-deficient and electron-rich dienophiles to give, via one-step hetero-Diels-Alder cycloaddition reactions, the corresponding 5H-coumarin[4,3-c]pyridin-5-ones. When excess of the dienophile was used, fused azatetracyclo, derivatives were also formed via a tandem Diels-Alder and 1,3-dipolar cycloaddition reaction of the dienophile to an azomethine ylide formed by the intermediate 2,3-dihydro-5H-coumarin[4,3-c]pyridine-5-one. The regio- and stereoselectivities of the new compounds correspond well with spectroscopic (2D NMR) and theoretical data. A possible mechanistic scheme is provided. (c) 2008 Elsevier Ltd. All rights reserved.
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