Bronsted acid-catalyzed rapid enol-ether formation of 2-hydroxyindole-3-carboxaldehydes

被引：6

作者：

Blanchard, Darian ^{[1
]}

Cameron, T. Stanley ^{[2
]}

Jha, Mukund ^{[1
]}

机构：

[1] Nipissing Univ, Dept Biol & Chem, North Bay, ON P1B 8L7, Canada

[2] Dalhousie Univ, Dept Chem, Halifax, NS B3H 4J3, Canada

来源：

MOLECULAR DIVERSITY | 2013年 / 17卷 / 04期

基金：

加拿大创新基金会; 加拿大自然科学与工程研究理事会;

关键词：

Indole; Heterocycles; 3-(Alkoxymethylene)indolin-2-one; Oxindole; Enol-ether; N-Bromosuccinimide; p-TSA; Trifluroacetic acid; N-BROMOSUCCINIMIDE; 2-(ALKYNYL)ARYL ISOCYANATES; OXINDOLE ALKALOIDS; ISATIS-COSTATA; EFFICIENT; DERIVATIVES; ALCOHOLS;

D O I：

10.1007/s11030-013-9470-x

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

A one-step Bronsted acid-catalyzed synthetic methodology leading to 3-(alkoxymethylene)indolin-2-ones was developed starting from easily accessible 2-hydroxyindole-3-carboxaldehydes. The procedure simply involves a treatment of differently substituted 2-hydroxyindole-3-carboxaldehydes with various alcohols (primary/secondary/tertiary/allyl/propargyl/benzyl) in the presence of a catalytic amount of Bronsted acids such as -toluenesulfonic acid and trifluroacetic acid. A series of 19 indolin-2-one-based enol-ethers were synthesized in excellent yields, which implies the general character of our methodology. The enol-ethers produced could be used as a useful building block for the synthesis of indole-based heterocycles.

引用

页码：827 / 834

页数：8

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