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Synfacts 2011(9): 0943-0943  
DOI: 10.1055/s-0030-1260992
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart ˙ New York

Copper-Catalyzed Synthesis of Pyrrolo[3,2-c]quinolin-4-nones

Contributor(s): Victor Snieckus, Yigang Zhao
F. Zhou, J. Liu, K. Ding, J. Liu, Q. Cai*
Guangzhou Institutes of Biomedicine and Health, P. R. of China
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Publication History

Publication Date:
19 August 2011 (online)

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Significance

A concise synthesis of pyrroloquinolinones is reported from the reaction of isocyanides and N-(o-haloaryl)propiolamides under copper-catalyzed conditions. A mechanism in which a copper-catalyzed [3+2] cycloaddition to form an organocopper species followed by an intramolecular C-C coupling involving N-(o-iodoaryl)propiol­amides is proposed. Good functional group compatibility was observed; however, for X = Br the reaction efficiency was greatly reduced.