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Synthesis 2011(18): 3037-3044  
DOI: 10.1055/s-0030-1260171
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© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of 4-Oxoindeno[1,2-b]pyrroles through Copper-Catalyzed Tandem Reactions of 1-(2-Haloaryl)enones with Isocyanides

Fengtao Zhou, Liangbing Fu, Jiajia Wie, Ke Ding, Qian Cai*
Key Laboratory of Regenerative Biology and Institute of Chemical Biology, Guangzhou Institutes of Biomedicine and Health, Chinese Academy of Sciences, No. 190, Kaiyuan Avenue, Science Park, Guangzhou, 510530, P. R. of China
Fax: +86(20)32015266; e-Mail: cai_qian@gibh.ac.cn;
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Publication History

Received 22 April 2011
Publication Date:
16 August 2011 (online)

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Abstract

Copper-catalyzed tandem reactions of 1-(2-haloaryl)­-enones with isocyanides for the synthesis of 4-oxoindeno[1,2-b]pyrroles are described. Highly reactive cyclic organocopper intermediates are generated in the copper-catalyzed [3+2]-cycloaddition reactions of isocyanides to double or triple bonds. Successful intramolecular trapping of the organocopper intermediates led to the efficient formation of 4-oxoindeno[1,2-b]pyrroles.

Key words

copper-catalyzed - isocyanide - enones - pyrroles

    Primary data for this article are available online and can be cited using the following DOI: 10.4125/pd0017th:
  • Primary Data
9

For details, see the Primary Data.

10

No fully substituted product 6 was detected without adding CuI as the catalyst.