Alanthadka, Anitha;
Devi, E. Sankari;
Nagarajan, Subbiah;
Sridharan, Vellaisamy;
Suvitha, Ambigapathy;
Maheswari, C. Uma
NHC‐Catalyzed Benzylic Csp³–H Bond Activation of Alkylarenes and N‐Benzylamines for the Synthesis of 3H‐Quinazolin‐4‐ones: Experimental and Theoretical Study
You can manage bookmarks using lists, please log in to your user account for this.
Media type:
E-Article
Title:
NHC‐Catalyzed Benzylic Csp³–H Bond Activation of Alkylarenes and N‐Benzylamines for the Synthesis of 3H‐Quinazolin‐4‐ones: Experimental and Theoretical Study
Contributor:
Alanthadka, Anitha;
Devi, E. Sankari;
Nagarajan, Subbiah;
Sridharan, Vellaisamy;
Suvitha, Ambigapathy;
Maheswari, C. Uma
Published:
Wiley, 2016
Published in:
European Journal of Organic Chemistry, 2016 (2016) 28, Seite 4872-4880
Description:
An N‐heterocyclic carbene catalyzed benzylic Csp³–H bond activation of alkylarenes and N‐benzylamines under metal‐free conditions was developed. This organocatalyzed oxidative transformation afforded the corresponding carbonyl derivatives in good to excellent yields. A variety of alkylarenes and N‐benzylamines were tolerated under the optimized reaction conditions. The established method was further extended to the synthesis of biologically important 3H‐quinazolin‐4‐ones in good yields. For example, NPS 53574, a potent calcium receptor antagonist, was successfully synthesized by using this oxidative protocol. DFT studies show that the benzylic C–H bond activation proceeds through the nucleophilic attack of the free carbene on the benzylic carbon atom.