Cargando…
An Efficient Solvent-Free Synthesis of 2-Hydroxy-2-(trifluoromethyl)-2H-chromenes Using Silica-Immobilized L-Proline
An efficient synthesis of 2-hydroxy-2-(trifluoromethyl)-2H-chromene-3-carboxylates was carried out under solvent-free conditions in an oven or microwave oven via the Knoevenagel condensation of salicylaldehydes with ethyl trifluoroacetoacetate followed by intramolecular cyclization in the presence o...
Autores principales: | , , , , , |
---|---|
Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2013
|
Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6290574/ https://www.ncbi.nlm.nih.gov/pubmed/24077175 http://dx.doi.org/10.3390/molecules181011964 |
_version_ | 1783380115186515968 |
---|---|
author | Xu, Cuilian Yang, Guoyu Wang, Caixia Fan, Sufang Xie, Lixia Gao, Ya |
author_facet | Xu, Cuilian Yang, Guoyu Wang, Caixia Fan, Sufang Xie, Lixia Gao, Ya |
author_sort | Xu, Cuilian |
collection | PubMed |
description | An efficient synthesis of 2-hydroxy-2-(trifluoromethyl)-2H-chromene-3-carboxylates was carried out under solvent-free conditions in an oven or microwave oven via the Knoevenagel condensation of salicylaldehydes with ethyl trifluoroacetoacetate followed by intramolecular cyclization in the presence of silica-immobilized L-proline. The structures of the title compounds were characterized by IR, (1)H-NMR, (13)C-NMR, HRMS and X-ray single crystal diffraction. The improved method described herein is economical, easily-operated and environmentally friendly. Furthermore, the catalyst can be recovered conveniently and reused without obvious loss of activity. |
format | Online Article Text |
id | pubmed-6290574 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2013 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-62905742018-12-20 An Efficient Solvent-Free Synthesis of 2-Hydroxy-2-(trifluoromethyl)-2H-chromenes Using Silica-Immobilized L-Proline Xu, Cuilian Yang, Guoyu Wang, Caixia Fan, Sufang Xie, Lixia Gao, Ya Molecules Article An efficient synthesis of 2-hydroxy-2-(trifluoromethyl)-2H-chromene-3-carboxylates was carried out under solvent-free conditions in an oven or microwave oven via the Knoevenagel condensation of salicylaldehydes with ethyl trifluoroacetoacetate followed by intramolecular cyclization in the presence of silica-immobilized L-proline. The structures of the title compounds were characterized by IR, (1)H-NMR, (13)C-NMR, HRMS and X-ray single crystal diffraction. The improved method described herein is economical, easily-operated and environmentally friendly. Furthermore, the catalyst can be recovered conveniently and reused without obvious loss of activity. MDPI 2013-09-26 /pmc/articles/PMC6290574/ /pubmed/24077175 http://dx.doi.org/10.3390/molecules181011964 Text en © 2013 by the authors; licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/). |
spellingShingle | Article Xu, Cuilian Yang, Guoyu Wang, Caixia Fan, Sufang Xie, Lixia Gao, Ya An Efficient Solvent-Free Synthesis of 2-Hydroxy-2-(trifluoromethyl)-2H-chromenes Using Silica-Immobilized L-Proline |
title | An Efficient Solvent-Free Synthesis of 2-Hydroxy-2-(trifluoromethyl)-2H-chromenes Using Silica-Immobilized L-Proline |
title_full | An Efficient Solvent-Free Synthesis of 2-Hydroxy-2-(trifluoromethyl)-2H-chromenes Using Silica-Immobilized L-Proline |
title_fullStr | An Efficient Solvent-Free Synthesis of 2-Hydroxy-2-(trifluoromethyl)-2H-chromenes Using Silica-Immobilized L-Proline |
title_full_unstemmed | An Efficient Solvent-Free Synthesis of 2-Hydroxy-2-(trifluoromethyl)-2H-chromenes Using Silica-Immobilized L-Proline |
title_short | An Efficient Solvent-Free Synthesis of 2-Hydroxy-2-(trifluoromethyl)-2H-chromenes Using Silica-Immobilized L-Proline |
title_sort | efficient solvent-free synthesis of 2-hydroxy-2-(trifluoromethyl)-2h-chromenes using silica-immobilized l-proline |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6290574/ https://www.ncbi.nlm.nih.gov/pubmed/24077175 http://dx.doi.org/10.3390/molecules181011964 |
work_keys_str_mv | AT xucuilian anefficientsolventfreesynthesisof2hydroxy2trifluoromethyl2hchromenesusingsilicaimmobilizedlproline AT yangguoyu anefficientsolventfreesynthesisof2hydroxy2trifluoromethyl2hchromenesusingsilicaimmobilizedlproline AT wangcaixia anefficientsolventfreesynthesisof2hydroxy2trifluoromethyl2hchromenesusingsilicaimmobilizedlproline AT fansufang anefficientsolventfreesynthesisof2hydroxy2trifluoromethyl2hchromenesusingsilicaimmobilizedlproline AT xielixia anefficientsolventfreesynthesisof2hydroxy2trifluoromethyl2hchromenesusingsilicaimmobilizedlproline AT gaoya anefficientsolventfreesynthesisof2hydroxy2trifluoromethyl2hchromenesusingsilicaimmobilizedlproline AT xucuilian efficientsolventfreesynthesisof2hydroxy2trifluoromethyl2hchromenesusingsilicaimmobilizedlproline AT yangguoyu efficientsolventfreesynthesisof2hydroxy2trifluoromethyl2hchromenesusingsilicaimmobilizedlproline AT wangcaixia efficientsolventfreesynthesisof2hydroxy2trifluoromethyl2hchromenesusingsilicaimmobilizedlproline AT fansufang efficientsolventfreesynthesisof2hydroxy2trifluoromethyl2hchromenesusingsilicaimmobilizedlproline AT xielixia efficientsolventfreesynthesisof2hydroxy2trifluoromethyl2hchromenesusingsilicaimmobilizedlproline AT gaoya efficientsolventfreesynthesisof2hydroxy2trifluoromethyl2hchromenesusingsilicaimmobilizedlproline |