Copper-Catalyzed Multicomponent Domino Reaction of 2-Bromoaldehydes, Benzylamines, and Sodium Azide for the Assembly of Quinazoline Derivatives

Abstract

An efficient three-component domino reaction of 2-bromoaldehydes, benzylamines, and sodium azide has been developed for the synthesis of quinazoline derivatives. This domino process involves copper-catalyzed SNAr, oxidation/cyclization, and denitrogenation sequences. The mild catalytic system enabled the effective construction of three C-N bonds in one operation.

Decorated Peptide Nanofibers with Cu Nanoparticles: An Efficient Catalyst for the Multicomponent Synthesis of Chromeno [2, 3‐d] pyrimidin‐8‐amines, Quinazolines and 2H‐ Indazoles

“…Also, we were successful to extend the scope of the reaction for the application of aliphatic amines such as benzylamine and 4‐methoxybenzylamine (Table , entries 8 and 9). Based on the previous reports,, a plausible pathway for the formation of (16) is described in Scheme . Initially, in the presence of CuNP‐PNF, 2‐halobenzaldehyde reacts with aniline to afford imine (17) .…”

“…CuFe 2 O 4 and CuI/L‐Proline . However, some of these catalysts or catalytic systems have some disadvantages such as long reaction times , harsh reaction conditions , use of hazardous organic solvents and expensive catalysts.…”

Cuprous Oxide Nanoparticle Supported on Iron Oxide (Cu2O-Fe3O4): Magnetically Separable and Reusable Nanocatalyst for the Synthesis of Quinazolines

“…On the basis of previous literature report and based on control experiment, a possible reaction mechanism has been illustrated in Scheme . Initially, the substrate 1a reacted with 2a to generate the (E)‐N‐(2‐bromobenzylidene)‐1‐phenylmethanamine intermediate A.…”

“…al . have synthesized quinazolines using 2‐bromobenzaldehydes and benzylamines with sodium azide in using CuI as catalyst and L‐proline as a suitable ligand in DMSO . Although this protocol work smoothly under mild condition and give very good yield of quinazolines, however there is still a need to recycle the catalyst and to carry out reaction under ligand free condition and in greener solvent.…”

The synthesis ofN‐containing heterocyclic compounds catalyzed by copper/L‐proline

“…In 2016, Wu's group utilized 2‐bromoaldehydes 149 , benzylamines 150 , and NaN 3 for the simple synthesis of quinazoline derivatives 151 by using CuI/ L ‐proline as the catalytic system (Scheme 25). [ 62 ] This transformation involved S N Ar, oxidation/cyclization and denitrogenation reaction sequences. When only CuI was used as the catalyst, the yield of product 151a decreased from 72% to 42%.…”