Synthesis of fused tetrahydro-beta-carbolinequinoxalinones in 1-n-butyl-2,3-dimethylimidazolium bis(trifluoromethylsulfonyl)imide ([bdmim][Tf2N]) and 1-n-butyl-2,3-dimethylimidazolium perfluorobutylsulfonate ([bdmim][PFBuSO3]) ionic liquids | Health & Environmental Research Online (HERO)

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Citation
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HERO ID

3857450

Reference Type

Journal Article

Title

Synthesis of fused tetrahydro-beta-carbolinequinoxalinones in 1-n-butyl-2,3-dimethylimidazolium bis(trifluoromethylsulfonyl)imide ([bdmim][Tf2N]) and 1-n-butyl-2,3-dimethylimidazolium perfluorobutylsulfonate ([bdmim][PFBuSO3]) ionic liquids

Author(s)

Tseng, MC; Liang, YM; Chu, YH

Year

2005

Is Peer Reviewed?

Journal

Tetrahedron Letters
ISSN: 0040-4039
EISSN: 1873-3581

Volume

Issue

Page Numbers

6131-6136

Language

English

DOI

10.1016/j.tetlet.2005.06.153

Web of Science Id

WOS:000231342000036

Abstract

Starting from tryptophan methyl ester, a three-step synthesis of fused tetrahydro-beta-carbolinequinoxalinones in two new ionic liquids, [bdmim][Tf2N] and [bdmim][PFBUSO3], was described. Both ionic liquids can be readily prepared from commercially available starting materials in high yields. Unlike the commonly used [PF6]-based ionic liquids that evidently undergo slow hydrolysis of the PF6 anion with the concomitant release of HF, ionic liquids of [bdmim][Tf2N] and [bdmim][PFBuSO3] are not only chemically stable but also apparently inert to hydrolysis and therefore organic reactions carried out in both ionic liquids proceed smoothly with good yields. The overall isolated yields for this three-step synthesis of tetrahydro-beta-carbolinequinoxalinones were 34-55%. To the best of our knowledge, the preparation of fused tetrahydro-beta-carbolinequinoxalinones was unprecedented. (c) 2005 Elsevier Ltd. All rights reserved.

Keywords

ionic liquid; organic synthesis; tetrahydro-beta-carbolinequinoxalmone