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
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
收藏
页码:2653 / 2660
页数:8
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