Please use this identifier to cite or link to this item:
https://doi.org/10.1002/chem.201300047
Title: | Highly regioselective organocatalyzed synthesis of pyrazoles from diazoacetates and carbonyl compounds | Authors: | Wang, L. Huang, J. Gong, X. Wang, J. |
Keywords: | cycloaddition enamines nitrogen heterocycles organocatalysis pyrazoles |
Issue Date: | 3-Jun-2013 | Citation: | Wang, L., Huang, J., Gong, X., Wang, J. (2013-06-03). Highly regioselective organocatalyzed synthesis of pyrazoles from diazoacetates and carbonyl compounds. Chemistry - A European Journal 19 (23) : 7555-7560. ScholarBank@NUS Repository. https://doi.org/10.1002/chem.201300047 | Abstract: | A general, organocatalytic inverse-electron-demand [3+2] cycloaddition reaction between a range of carbonyl compounds and diazoacetates has been developed. This reaction is catalyzed by secondary amines as a "green promoter" to generate substituted pyrazoles with high levels of regioselectivity. It is noteworthy that this [3+2] cycloaddition reaction proceeds efficiently at room temperature with a simple and inexpensive catalyst. Considering the large variety and ready availability of the starting materials (e.g. ketones, β-ketoesters, β-diketones, and aldehydes), as well as the operational simplicity of this process, a convenient, practical, and highly modular pyrazole synthesis has been developed. We believe that this work will arouse more research interest in the organocatalytic synthesis of other biologically active heterocycles. Such studies are currently underway in our laboratory. Dipoles apart: In situ formed enamines react with diazoacetates under mild conditions to afford the corresponding polysubstituted pyrazoles in good-to-excellent yields through an inverse-electron-demand 1,3-dipolar cycloaddition process (see scheme). Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. | Source Title: | Chemistry - A European Journal | URI: | http://scholarbank.nus.edu.sg/handle/10635/76308 | ISSN: | 09476539 | DOI: | 10.1002/chem.201300047 |
Appears in Collections: | Staff Publications |
Show full item record
Files in This Item:
There are no files associated with this item.
Items in DSpace are protected by copyright, with all rights reserved, unless otherwise indicated.