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Controllable Synthesis of Pyrido[2,3-b]indol-4-ones or Indolo[3,2-b]quinolines via Formal Intramolecular C(sp2)-H Functionalization

Abstract

A novel Fe-catalyzed protocol for the controllable synthesis of pyrido[2,3-b]indol-4-ones or indolo[3,2-b]quinolines has been developed by using indole-2-carboxylic derivatives as starting materials. Indole-2-carboxenamines were transformed into pyrido[2,3-b]indol-4-ones through intramolecular N−H/C−H coupling, in which a carbonyl 1,2-migration was involved. Whereas, when indole-2-carboxarylamines were employed, indolo[3,2-b]quinolones were produced through direct N−H/C−H coupling. The desired products were obtained under mild reaction conditions in moderate to good yields with wide substrate scope. The natural product quindolinone was conveniently prepared by this reaction.

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Publication details

The article was received on 29 Sep 2019, accepted on 08 Nov 2019 and first published on 09 Nov 2019


Article type: Paper
DOI: 10.1039/C9OB02108F
Org. Biomol. Chem., 2019, Accepted Manuscript

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    Controllable Synthesis of Pyrido[2,3-b]indol-4-ones or Indolo[3,2-b]quinolines via Formal Intramolecular C(sp2)-H Functionalization

    B. Song, M. Wang, M. Xu, L. Kong, H. Xie, C. Wang and Y. LI, Org. Biomol. Chem., 2019, Accepted Manuscript , DOI: 10.1039/C9OB02108F

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