Elsevier

Tetrahedron Letters

Volume 50, Issue 4, 28 January 2009, Pages 448-451
Tetrahedron Letters

Unexpected one-pot synthesis of new polycyclic coumarin[4,3-c]pyridine derivatives via a tandem hetero-Diels–Alder and 1,3-dipolar cycloaddition reaction

https://doi.org/10.1016/j.tetlet.2008.11.033Get rights and content

Abstract

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.

Graphical abstract

O-Methyl-4-coumarincarboxaldehyde oxime reacted with electron-deficient and electron-rich dienophiles to give, in one step, coumarin[4,3-c]pyridine derivatives. The regio- and stereoselectivities of the new compounds correspond well with spectroscopic and theoretical data. A possible mechanistic scheme is provided.

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Acknowledgments

D.R. Gautam thanks State Scholarships Foundation (IKY), Greece, for financial support and Tribhuvan University, Katmandu, Nepal, for granting him the PhD study leave.

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