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Generation of diverse 1-imidazolylisoquinolines via silver triflate-catalyzed reaction of 2-alkynylbenzaldoxime with imidazole

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Abstract

Diverse 1-imidazolylisoquinolines are generated through a silver triflate-catalyzed cascade reaction of 2-alkynylbenzaldoxime with imidazole or benzoimidazole using parallel diversity-oriented synthesis. A small library of 1-imidazolylisoquinolines can be constructed efficiently under mild conditions. A plausible mechanism is proposed. We discovered that the presence of silver triflate and bromotrispyrrolidinophosphonium hexafluorophosphate (PyBroP) is essential for the reaction transformation. In the reaction process, treatment of 2-alkynylbenzaldoxime with silver triflate affords isoquinoline-N-oxide. Then, isoquinoline-N-oxide acts as a nucleophile to attack PyBroP to replace the bromide. Subsequently, an intermolecular nucleophilic addition of imidazole and further deprotonation take place to produce the desired 1-imidazolylisoquinolines. A range of great diversity could be easily introduced under the standard conditions during the reaction process.

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Authors and Affiliations

  1. Department of Chemistry, Nanchang University, 999 Xuefu Road, Nanchang, 330031, Jiangxi, China

    Qian Xiao & Ling Zhang

  2. Department of Chemistry, Fudan University, 220 Handan Road, Shanghai, 200433, China

    Shengqing Ye, Danqing Zheng & Jie Wu

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  1. Qian Xiao
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  2. Shengqing Ye
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  3. Danqing Zheng
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  4. Ling Zhang
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  5. Jie Wu
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Correspondence to Ling Zhang or Jie Wu.

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Xiao, Q., Ye, S., Zheng, D. et al. Generation of diverse 1-imidazolylisoquinolines via silver triflate-catalyzed reaction of 2-alkynylbenzaldoxime with imidazole. Mol Divers 16, 261–268 (2012). https://doi.org/10.1007/s11030-012-9355-4

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  • DOI: https://doi.org/10.1007/s11030-012-9355-4

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