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Issue 84, 2018
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Molecular iodine-mediated formal [2+1+1+1] cycloaddition access to pyrrolo[2,1-a]isoquinolines with DMSO as the methylene source

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Abstract

A molecular iodine-mediated formal [2+1+1+1] cycloaddition for the efficient synthesis of pyrrolo[2,1-a]isoquinolines from acetophenones, 1,2,3,4-tetrahydroisoquinoline (THIQ) and DMSO has been developed. Mechanistic studies revealed that DMSO served as the methylene source, and this novel protocol involves intermolecular cycloaddition of two in situ generated intermediates that enable efficient formation of one C–N bond and three C–C bonds via multiple sequential C–H functionalizations.

Graphical abstract: Molecular iodine-mediated formal [2+1+1+1] cycloaddition access to pyrrolo[2,1-a]isoquinolines with DMSO as the methylene source

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Publication details

The article was received on 25 Aug 2018, accepted on 25 Sep 2018 and first published on 01 Oct 2018


Article type: Communication
DOI: 10.1039/C8CC06908E
Citation: Chem. Commun., 2018,54, 11897-11900
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    Molecular iodine-mediated formal [2+1+1+1] cycloaddition access to pyrrolo[2,1-a]isoquinolines with DMSO as the methylene source

    K. Zheng, S. Zhuang, W. Shu, Y. Wu, C. Yang and A. Wu, Chem. Commun., 2018, 54, 11897
    DOI: 10.1039/C8CC06908E

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