title: Bicyclic 1,2,3-triazolium ionic liquids: synthesis, characterization, and application to rutaecarpine synthesis.
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.
authors.affiliation: Department of Chemistry and Biochemistry, National Chung Cheng University, 168 University Road, Minhsiung, Chiayi 62102, Taiwan, ROC.
authors.forename: Ming-Chung
authors.initials: MC
authors.lastname: Tseng
authors.forename: Hui-Ting
authors.initials: HT
authors.lastname: Cheng
authors.forename: Meng-Jane
authors.initials: MJ
authors.lastname: Shen
authors.forename: Yen-Ho
authors.initials: YH
authors.lastname: Chu
mesh_terms: D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000737:chemistry*; D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D052578:Ionic Liquids / Q000737:chemistry*; D015394:Molecular Structure; D011799:Quinazolines / Q000138:chemical synthesis* / Q000737:chemistry; D014230:Triazoles / Q000737:chemistry*; D052999:Quinazolinones
chemical_list: D019086:Bridged Bicyclo Compounds, Heterocyclic; D026121:Indole Alkaloids; D052578:Ionic Liquids; D011799:Quinazolines; D014230:Triazoles; C028632:rutecarpine; D052999:Quinazolinones