Synthesis of α-Carbolines Starting from 2,3-Dichloropyridines and Substituted Anilines

被引：74

作者：

Hostyn, Steven ^{[1
]}

Van Baelen, Gitte ^{[1
]}

Lemiere, Guy L. F. ^{[1
]}

Maes, Bert U. W. ^{[1
]}

机构：

[1] Univ Antwerp, Dept Chem, B-2020 Antwerp, Belgium

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2008年 / 350卷 / 16期

关键词：

alpha-carbolines; C-H activation; direct arylation; malaria; microwave heating; palladium;

D O I：

10.1002/adsc.200800077

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

9H-alpha-Carbolines have been prepared via consecutive intermolecular Buchwald-Hartwig reaction and Pd-catalyzed intramolecular direct arylation from commercially available 2,3-dichloropyridines and substituted anilines. The combination of a high reaction temperature (180 degrees C) and the use of DBU were found to be crucial for the intramolecular direct arylation reactions of the 3-cliloro-N-phenylpyridin-2-amines as no reaction was observed at 120 degrees C and 180 degrees C using different inorganic and other organic bases. On the other hand, nitrogenmethylated pyridine analogues of these substrates {N-[3-chloro-l-methylpyridin-2(1H)-ylidene]anilines} do undergo ring closure at 120 degrees C, with K3PO4 as base, affording the respective 1-methyl-1H-alpha-carbolines in good yields.

引用

页码：2653 / 2660

页数：8

共 72 条

[71] In vitro inhibition of β-haematin formation, DNA interactions, antiplasmodial activity, and cytotoxicity of synthetic neocryptolepine derivatives [J].