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Applications of ortho-phenylisonitrile and ortho-N-Boc aniline for the two-step preparation of novel bis-heterocyclic chemotypes

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Abstract

Concise routes to five pharmacologically relevant bis-heterocyclic scaffolds are described. Significant molecular complexity is generated in a mere two synthetic operations enabling access to each scaffold. Routes are often improved by microwave irradiation and all utilize isocyanide-based multi-component reaction methods to incorporate the required diversity elements. Common reagents in all initial condensation reactions include 2-(N-Boc-amino)-phenyl-isocyanide 1, mono-Boc-phenylenediamine 2 and ethyl glyoxalate 3.

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Authors and Affiliations

  1. College of Pharmacy, The University of Arizona, BIO5 Oro Valley, 1580 E. Hanley Blvd, Oro Valley, AZ, 85737, USA

    Zhigang Xu, Arthur Y. Shaw & Christopher Hulme

  2. Department of Chemistry and Biochemistry, The University of Arizona, Tucson, AZ, USA

    Gary S. Nichol, Alexandra P. Cappelli & Christopher Hulme

Authors
  1. Zhigang Xu
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  2. Arthur Y. Shaw
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  3. Gary S. Nichol
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  4. Alexandra P. Cappelli
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  5. Christopher Hulme
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Corresponding author

Correspondence to Christopher Hulme.

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Xu, Z., Shaw, A.Y., Nichol, G.S. et al. Applications of ortho-phenylisonitrile and ortho-N-Boc aniline for the two-step preparation of novel bis-heterocyclic chemotypes. Mol Divers 16, 607–612 (2012). https://doi.org/10.1007/s11030-012-9374-1

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  • DOI: https://doi.org/10.1007/s11030-012-9374-1

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