共 72 条
Synthesis of α-Carbolines Starting from 2,3-Dichloropyridines and Substituted Anilines
被引:74
作者:

Hostyn, Steven
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机构:
Univ Antwerp, Dept Chem, B-2020 Antwerp, Belgium Univ Antwerp, Dept Chem, B-2020 Antwerp, Belgium

Van Baelen, Gitte
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h-index: 0
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Univ Antwerp, Dept Chem, B-2020 Antwerp, Belgium Univ Antwerp, Dept Chem, B-2020 Antwerp, Belgium

Lemiere, Guy L. F.
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Univ Antwerp, Dept Chem, B-2020 Antwerp, Belgium Univ Antwerp, Dept Chem, B-2020 Antwerp, Belgium

Maes, Bert U. W.
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机构:
Univ Antwerp, Dept Chem, B-2020 Antwerp, Belgium Univ Antwerp, Dept Chem, B-2020 Antwerp, Belgium
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.
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页码:2653 / 2660
页数:8
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