Elsevier

Tetrahedron Letters

Volume 46, Issue 21, 23 May 2005, Pages 3653-3656
Tetrahedron Letters

Studies into the generation and Diels–Alder reactions of 7,8-quinolyne with furan dienes

https://doi.org/10.1016/j.tetlet.2005.03.164Get rights and content

Abstract

Reaction of an appropriate ortho-halo tosylate precursor with organolithium reagents provides the first conclusive route to the intermediate, 7,8-quinolyne. The transient existence of this hetaryne was confirmed by Diels–Alder reactions with furan derivatives that provide endoxide adducts. Chemical induced rearrangement of these adducts allows entry to key compounds of 10-hydroxy[h]benzoquinoline and its 7-substituted derivatives in modest yields.

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Acknowledgements

The authors would like to thank the Materials Control Program of Los Alamos National Laboratory for funding and Professor D. Wege for helpful discussions.

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