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 |
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Hauptverfasser: | , , , , |
Format: | Artikel |
Sprache: | eng |
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Online-Zugang: | Volltext |
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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. |
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ISSN: | 0022-3263 1520-6904 |
DOI: | 10.1021/jo2006939 |