Title
Synthesis of α-carbolines starting from 2,3-dichloropyridines and substituted anilines Synthesis of α-carbolines starting from 2,3-dichloropyridines and substituted anilines
Author
Faculty/Department
Faculty of Sciences. Chemistry
Publication type
article
Publication
Weinheim ,
Subject
Chemistry
Source (journal)
Advanced synthesis and catalysis. - Weinheim
Volume/pages
350(2008) :16 , p. 2653-2660
ISSN
1615-4150
ISI
000261325500026
Carrier
E
Target language
English (eng)
Full text (Publishers DOI)
Affiliation
University of Antwerp
Abstract
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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