Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2019, Issue 30, Pages 4928-4940Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201900880
Keywords
Heterogeneous catalysis; Imidazolium salt; Nitrogen heterocycles; Sustainable chemistry; Synthetic methods
Categories
Funding
- University of Alicante [VIGROB-173, VIGROB-285, VIGROB-316]
- Spanish Ministerio de Economia y Competitividad [CTQ2015-66624-P, CTQ2017-88171-P]
- Spanish Ministerio de Ciencia, Innovacion y Universidades [PGC2018-096616-B-I00]
- Generalitat Valenciana [AICO/2017/007]
- Spanish Ministerio de Educacion, Cultura y Deporte [FPU15/06040]
- ISO (University of Alicante)
Ask authors/readers for more resources
Quinoline and acridine derivatives have been prepared using a functionalized imidazolium salt as heterogeneous catalyst. Different ketones have been coupled with 2-aminobenzaldehydes and 2-aminoaryl ketones under solvent-free conditions, employing 1,3-bis(carboxymethyl)-imidazolium chloride as a catalyst. The protocol is simple and effective for the synthesis of a variety of nitrogen containing heterocycles (> 35 examples) with moderate to excellent yields (up to 96 %), being possible to perform the reaction in preparative scale. Additionally, 3-acetylquinolines have been transformed, under solvent-free conditions, into quinolyl chalcone derivatives by means of the same catalyst. Thus, the catalytic system mediates both reactions effectively in a tandem procedure. Furthermore, the catalyst is easily separated from the reaction mixture and can be reused without loss of activity (up to 8 cycles) which remarks its sturdiness. The E-factors are in the range of 14-23, both for the formation of quinolines and for the tandem reaction, which demonstrates the sustainability of the protocols described.
Authors
I am an author on this paper
Click your name to claim this paper and add it to your profile.
Reviews
Recommended
No Data Available