Biomaterial Database

Bicyclic 1,2,3-triazolium ionic liquids: synthesis, characterization, and application to rutaecarpine synthesis. 2011

Ming-Chung Tseng, and Hui-Ting Cheng, and Meng-Jane Shen, and Yen-Ho Chu

Department of Chemistry and Biochemistry, National Chung Cheng University, 168 University Road, Minhsiung, Chiayi 62102, Taiwan, ROC.

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.

UI	MeSH Term	Description	Entries
D011799	Quinazolines	A group of aromatic heterocyclic compounds that contain a bicyclic structure with two fused six-membered aromatic rings, a benzene ring and a pyrimidine ring.	Quinazoline
D014230	Triazoles	Heterocyclic compounds containing a five-membered ring with two carbon atoms and three nitrogen atoms with the molecular formula C2H3N3.	Triazole
D015394	Molecular Structure	The location of the atoms, groups or ions relative to one another in a molecule, as well as the number, type and location of covalent bonds.	Structure, Molecular,Molecular Structures,Structures, Molecular
D052578	Ionic Liquids	Salts that melt below 100 C. Their low VOLATILIZATION can be an advantage over volatile organic solvents.	Ionic Liquid,Ionic Solvents,Liquid, Ionic,Liquids, Ionic,Solvents, Ionic
D019086	Bridged Bicyclo Compounds, Heterocyclic	Heterocyclic compounds that contain two rings that share two non-adjacent atoms in common.	Bicyclo Compounds, Heterocyclic,Heterocyclic Cpds, Bicyclic,Bicyclic Heterocyclic Compounds,Heterocyclic Bicyclo Compounds,Bicyclic Heterocyclic Cpds,Heterocyclic Compounds, Bicyclic
D026121	Indole Alkaloids	Group of alkaloids containing a benzylpyrrole group (derived from TRYPTOPHAN).	Indole Alkaloid,Alkaloid, Indole,Alkaloids, Indole