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

[Display omitted] 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...

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Bibliographic Details
Published in:Tetrahedron letters 2005-05, Vol.46 (21), p.3653-3656
Main Authors: Collis, Gavin E., Burrell, Anthony K.
Format: Article
Language:English
Subjects:
7,8-Quinolyne
Benzo[ h]quinoline
Diels–Alder reaction
Endoxide rearrangement
Furan
Hetaryne
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Summary:[Display omitted] 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.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2005.03.164