To use all functions of this page, please activate cookies in your browser.
With an accout for my.chemeurope.com you can always see everything at a glance – and you can configure your own website and individual newsletter.
- My watch list
- My saved searches
- My saved topics
- My newsletter
The Biginelli reaction is a multiple-component chemical reaction that creates 3,4-dihydropyrimidin-2(1H)-ones 4 from ethyl acetoacetate 1, an aryl aldehyde (such as benzaldehyde 2), and urea 3. It is named for the Italian chemist Pietro Biginelli.
This reaction was developed by Pietro Biginelli in 1891. The reaction can be catalyzed by Brønsted acids and/or by Lewis acids such as boron trifluoride. Several solid-phase protocols utilizing different linker combinations have been published.
Additional recommended knowledge
The reaction mechanism of the Biginelli reaction is a series of bimolecular reactions leading to the desired dihydropyrimidinone.
The aldol condensation of ethylacetoacetate 1 and the aryl aldehyde is the rate-limiting step leading to the carbenium ion 2. The nucleophilic addition of urea gives the intermediate 4, which quickly dehydrates to give the desired product 5.
In 1987, Atwal et al.reported a modification to the Biginelli reaction that consistently generated higher yields.
|This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Biginelli_reaction". A list of authors is available in Wikipedia.|