ADDITION OF AMINES TO METHYL 3-DEHYDROQUINATE AND 3-DEHYDROSHIKIMATE

被引：7

作者：

BALTAS, M ^{[1
]}

DESPEYROUX, P ^{[1
]}

GORRICHON, L ^{[1
]}

机构：

[1] UNIV TOULOUSE 3, CNRS, SYNTH & PHYSICOCHIM ORGAN LAB, 118 ROUTE NARBONNE, F-31062 TOULOUSE, FRANCE

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 1993年 / 3卷 / 07期

关键词：

D O I：

10.1016/S0960-894X(01)80427-3

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Reaction of 3-dehydroquinate compounds 1-3 with primary amines is studied in CH2Cl2 and MeOH. The reaction yields 3-dehydroshikimate 4 (in CH2Cl2) and(or) 3-alkylamino 4-hydroxybenzoate derivatives 6 or 7. The results support a Schiff base formation and an intramolecular catalysis by a specific diamine [2-(2-(aminoethyl)pyridine]. The effects of the imine intermediate and of the solvent on the aromatization reaction are discussed.

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页码：1447 / 1452

页数：6

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