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Title
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Synthesis of α-carbolines starting from 2,3-dichloropyridines and substituted anilines
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Author
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Abstract
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| 9H--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 °C) and the use of DBU were found to be crucial for the intramolecular direct arylation reactions of the 3-chloro-N-phenylpyridin-2-amines as no reaction was observed at 120 °C and 180 °C using different inorganic and other organic bases. On the other hand, nitrogen-methylated pyridine analogues of these substrates {N-[3-chloro-1-methylpyridin-2(1H)-ylidene]anilines} do undergo ring closure at 120 °C, with K3PO4 as base, affording the respective 1-methyl-1H--carbolines in good yields. |
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Language
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English
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Source (journal)
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Advanced synthesis and catalysis. - Weinheim, 2001, currens
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Publication
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Weinheim
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2008
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ISSN
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1615-4150
[print]
1615-4169
[online]
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DOI
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10.1002/ADSC.200800077
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Volume/pages
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350
:16
(2008)
, p. 2653-2660
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ISI
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000261325500026
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Full text (Publisher's DOI)
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