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Synthesis of Aza-Fused Isoquinolines through Domino Cross-Aldol Condensation and Palladium-Catalyzed Intramolecular Direct Arylation

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    Synthesis of Aza-Fused Isoquinolines through Domino Cross-Aldol Condensation and Palladium-Catalyzed Intramolecular Direct Arylation
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    Department of Chemistry, Birla Institute of Technology and Science, Pilani, 333031 Rajasthan, India
    *A.K.: tel, +91-1596-515514; fax, +91-1596-244183; e-mail, [email protected]
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    The Journal of Organic Chemistry

    Cite this: J. Org. Chem. 2014, 79, 16, 7399–7404
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    https://doi.org/10.1021/jo501119f
    Published July 21, 2014
    Copyright © 2014 American Chemical Society
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    Abstract

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    A straightforward method has been developed for the synthesis of aroyl-substituted imidazo-/benzimidazo-fused isoquinolines. The cascade reaction proceeds via a cross-aldol condensation of 2-(1H-imidazol-1-yl/benzimidazolyl-1-yl)-1-arylethanones and 2-bromobenzaldehyde followed by palladium-catalyzed intramolecular C–H functionalization. This approach offers a simple and efficient alternative one-pot protocol for the assembly of imidazo/benzimidazo[2,1-a]isoquinolines in moderate to good yields.

    Copyright © 2014 American Chemical Society

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    Figures giving 1H NMR and 13C NMR spectra for compounds 3a–r. This material is available free of charge via the Internet at http://pubs.acs.org.

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    The Journal of Organic Chemistry

    Cite this: J. Org. Chem. 2014, 79, 16, 7399–7404
    Click to copy citationCitation copied!
    https://doi.org/10.1021/jo501119f
    Published July 21, 2014
    Copyright © 2014 American Chemical Society
    Request reuse permissions

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