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Issue 73, 2018
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Diversity-oriented synthesis of imidazo[2,1-a]isoquinolines

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Abstract

Herein, we report an efficient and practical strategy for the synthesis of five types of imidazo[2,1-a]isoquinolines via Cp*RhIII-catalyzed [4+2] annulation of 2-arylimidazoles and α-diazoketoesters, whose structural and substituted diversity at 5- or 6-position can be precisely controlled by the α-diazoketoester coupling partners. Compared with previous reports, in this study, we merged two attractive C–C cleavage strategies (retro-Claisen and decarboxylation) into the classical C–H functionalization/condensation process by choosing appropriate ester groups (–COOEt, –COOtBu or –COOiPr) or inexpensive additives (HOAc or KOAc). Moreover, the synthetic efficacies of these methods were demonstrated by the concise synthesis of several bioactive compounds and the late-stage modification of representative drugs.

Graphical abstract: Diversity-oriented synthesis of imidazo[2,1-a]isoquinolines

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Publication details

The article was received on 04 Jul 2018, accepted on 19 Jul 2018 and first published on 19 Jul 2018


Article type: Communication
DOI: 10.1039/C8CC05390A
Citation: Chem. Commun., 2018,54, 10240-10243

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    Diversity-oriented synthesis of imidazo[2,1-a]isoquinolines

    S. Mai, Y. Luo, X. Huang, Z. Shu, B. Li, Y. Lan and Q. Song, Chem. Commun., 2018, 54, 10240
    DOI: 10.1039/C8CC05390A

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