Copper-Catalyzed Tandem Reaction of Isocyanides with N-(2-Haloaryl)propiolamides for the Synthesis of Pyrrolo[3,2-c]quinolin-4-ones

The copper-catalyzed tandem reaction of isocyanides with N-(2-haloaryl)propiolamides is very efficient for the synthesis of pyrrolo[3, 2-c]quinolin-4-ones. Highly reactive cyclic organocopper intermediates were proposed to be generated in the copper-catalyzed formal [3 + 2] cycloaddition reaction of...

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Veröffentlicht in:Journal of organic chemistry 2011-07, Vol.76 (13), p.5346-5353
Hauptverfasser: Zhou, Fengtao, Liu, Jianguang, Ding, Ke, Liu, Jinsong, Cai, Qian
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Sprache:eng
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Zusammenfassung:The copper-catalyzed tandem reaction of isocyanides with N-(2-haloaryl)propiolamides is very efficient for the synthesis of pyrrolo[3, 2-c]quinolin-4-ones. Highly reactive cyclic organocopper intermediates were proposed to be generated in the copper-catalyzed formal [3 + 2] cycloaddition reaction of isocyanides with triple bonds. Intramolecular trapping of the organocopper intermediates can lead to aryl C–C bond formation, which offered an efficient method for constructing fused pyrrole structures.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo2006939