Hydrogen Transfer-Mediated Multicomponent Reaction for Direct Synthesis of Quinazolines by a Naphthyridine-Based Iridium Catalyst.

ABSTRACT: Selective linkage of renewable alcohols and ammonia into functional products would not only eliminate the prepreparation steps to generate active amino agents but also help in the conservation of our finite fossil carbon resources and contribute to the reduction of CO₂ emission. Herein the development of a novel 2-(4-methoxyphenyl)-1,8-naphthyridine-based iridium (III) complex is reported, which exhibits excellent catalytic performance toward a new hydrogen transfer-mediated annulation reaction of 2-nitrobenzylic alcohols with alcohols and ammonia. The catalytic transformation proceeds with the striking features of good substrate and functional group compatibility, high step and atom efficiency, no need for additional reductants, and liberation of H₂O as the sole by-product, which endows a new platform for direct access to valuable quinazolines. Mechanistic investigations suggest that the non-coordinated N-atom in the ligand serves as a side arm to significantly promote the condensation process by hydrogen bonding.

SUBMITTER: Tan Z 

PROVIDER: S-EPMC7150509 | biostudies-literature | 2020 Apr

REPOSITORIES: biostudies-literature