Tetrahedron letters

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

GE Collis, AK Burrell

Index: Collis, Gavin E.; Burrell, Anthony K. Tetrahedron Letters, 2005 , vol. 46, # 21 p. 3653 - 3656

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Citation Number: 13

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 ...