Tetrahedron Letters

Selective reduction. Reaction of 3, 4-dicarbomethoxyquinoline with lithium aluminium hydride. Steric effect.

A Godard, G Queguiner

Index: Godard, A.; Queguiner, G. Tetrahedron Letters, 1981 , vol. 22, # 48 p. 4813 - 4814

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Citation Number: 3

Abstract

Abstract The selective reduction of 3, 4-dicarbomethoxyquinoline by lithium aluminium hydride at low temperature affords only the unexpected 3-formyl 4-carbomethoxy quinoline. The difficulty of reduction of the usually more reactive 4-ester group can be explained by a steric hindrance by the H 5, peri proton on one side and by the 3-ester group on the other side.