Applications of counter-current chromatography in organic synthesis purification of heterocyclic derivatives of lapachol
| Autor: | Raphael S. F. Silva, Thiago B. Brum, Gilda Guimarães Leitão, Ana Paula G. Lobato, Antonio V. Pinto, Maria do Carmo F. R. Pinto |
|---|---|
| Rok vydání: | 2006 |
| Předmět: |
Chromatography
Molecular Structure Silica gel Elution Organic Chemistry Imidazoles General Medicine Biochemistry Analytical Chemistry Activating Transcription Factor 6 chemistry.chemical_compound Countercurrent chromatography Column chromatography Quinoxaline chemistry Cyclization Quinoxalines Organic chemistry Organic synthesis Chromatography Thin Layer Countercurrent Distribution Oxazoles Lapachol Oxazole Naphthoquinones |
| Zdroj: | Journal of chromatography. A. 1151(1-2) |
| ISSN: | 0021-9673 |
| Popis: | This work describes the application of counter-current chromatography (CCC) as a useful, fast and economic alternative for the isolation and purification of heterocyclic derivatives from lapachol and beta-lapachone, two naturally occurring compounds from Tabebuia species, and nor-beta-lapachone, a synthetic congener of lapachol. The discussed data comprise four examples of purification of synthetic reactions with different solvent systems - the mixture of the oxazole and the imidazole from beta-lapachone; the quinoxaline from nor-beta-lapachone; and the purification of the N-oxides from the quinoxaline and the phenazine from nor-beta-lapachone from their respective not fully reacted substrates by means of aqueous reversed- and normal-phase elution modes and non-aqueous solvent systems. Traditional purification of these reaction products by silica gel column chromatography demanded a large amount of solvent and time and, in some cases, serious degradation of the products occurred, leading to low yield of the reaction. High-speed counter-current chromatography (HSCCC) was used as an alternative to optimize the process and raise the yield of the reactions. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|
Full Text from ScienceDirect