Related Experiment Video
Updated: Aug 13, 2025

Facile Preparation of 4-Substituted Quinazoline Derivatives
Published on: February 15, 2016
Carbene-Catalyzed Activation of 2-Aminobenzaldehyde for Access to Chiral Fluorescent Quinazolinone
Tiantian Li1, Han Xiao1, Renjun Tian1
1Center for Industrial Catalysis & Cleaning Process Development, School of Chemical Engineering, Guizhou Minzu University, Huaxi District, Guiyang 550025, China.
Abstract:
A carbene-catalyzed reaction to synthesize a chiral quinazolinone with a new activation mode of an "aniline-like" N-H moiety is disclosed. Addition of the nitrogen atom of diphenyl o-aminobenzaldehydes via NHC activation to imines leads to chiral quinazolinones with high yields and optical purities. The acidity of the N-H moiety was extremely increased through the formation of an acyl azolium intermediate, which was investigated by DFT calculations. Moreover, the chiral quinazolinones were found to have high fluorescence quantum efficiency.
More Related Videos
14:11Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach
Published on: June 10, 2021
10:10Application of Elemental Lanthanides in the Selective C-F Activation of Trifluoromethylated Benzofulvenes Providing Access to Various Difluoroalkenes
Published on: July 28, 2018
Related Concept Videos
Nucleophilic Aromatic Substitution: Elimination–Addition
Preparation of 1° Amines: Hofmann and Curtius Rearrangement Overview
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions
Ketones with Nonenolizable Aromatic Aldehydes: Claisen–Schmidt Condensation
As the self-condensation of ketones is generally not favored in basic conditions, the self-condensed products do not form in the reaction between ketones and benzaldehyde. The general reaction of Claisen–Schmidt...
Electrophilic Aromatic Substitution: Fluorination and Iodination of Benzene