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  • Title: Bicyclic 1,2,3-triazolium ionic liquids: synthesis, characterization, and application to rutaecarpine synthesis.
    Author: Tseng MC, Cheng HT, Shen MJ, Chu YH.
    Journal: Org Lett; 2011 Aug 19; 13(16):4434-7. PubMed ID: 21797204.
    Abstract:
    Starting with commercial reagents, bicyclic 1,2,3-triazolium ionic liquids [b-3C-tr][NTf(2)] (1) and [b-4C-tr][NTf(2)] (2) were synthesized in four steps with high overall isolated yields of 68% and 76%, respectively. Since the C-5 hydrogen is acidic, under basic condition ionic liquids 1 and 2 were readily methylated with methyl iodide to afford chemically stable ionic liquids 7 and 8 at room temperature (88% and 82%, respectively). Ionic liquid 1 was used as the ionic solvent to demonstrate its usefulness for the synthesis of rutaecarpine, a natural product.
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