NaN(SiMe<sub>3</sub>)<sub>2</sub>/CsTFA Copromoted Aminobenzylation/Cyclization of 2-Isocyanobenzaldehydes with Toluene Derivatives or Benzyl Compounds: One-Pot Access to Dihydroquinazolines and Quinazolines
Xianghe Meng, Xue‐Cen Xu, Zhuo Wang, Yong‐Xin Liang, Yu‐Long Zhao
Abstract
A NaN(SiMe3)2/CsTFA copromoted aminobenzylation/cyclization reaction of 2-isocyanobenzaldehydes with toluene derivatives or benzyl compounds has been developed. The reaction works with a broad range of toluene derivatives and benzyl compounds, and provides a simple and efficient strategy for the synthesis of 4-benzyl-substitued dihydroquinazoline and quinazoline derivatives from easily available acyclic starting materials in a single step. Further applications, including synthesis of quinazoline, dihydroindolo[1,2-c]quinazoline, and dihydro-8H-isoquinolino[2,3-c]quinazoline, demonstrated the tremendous potential of the tandem reaction.
Topics & Concepts
ChemistryTolueneQuinazolineTandemCombinatorial chemistryReaction conditionsOrganic chemistryMedicinal chemistryCatalysisMaterials scienceComposite materialQuinazolinone synthesis and applicationsCatalytic C–H Functionalization MethodsN-Heterocyclic Carbenes in Organic and Inorganic Chemistry