<scp>TBHP‐Mediated</scp> Oxidative Decarboxylative Cyclization in Water: Direct and Sustainable Access to Anti‐malarial Polycyclic Fused Quinazolinones and Rutaecarpine
Nanjun Chen, Fei Xia, Yifan Zhao, Ji Ma, Yue Ma, Dong Zhang, Lan Yang, Peng Sun
Abstract
Summary of main observation and conclusion Polycyclic fused quinazolinones with anti‐malarial activity were synthesized through tert ‐butyl hydroperoxide (TBHP)‐mediated oxidative decarboxylative cyclization between commercially available isatins and cyclic amines in one step. The reaction proceeds smoothly in water without additional transition‐metal catalyst, acid and base. The newly synthesized products were evaluated to exhibit moderate to good anti‐malarial activity against chloroquine drug‐sensitive Plasmodium falciparum 3D7 strain. Additionally, this method also provides direct approach to Rutaecarpine in good yield.
Topics & Concepts
ChemistryRutaecarpinePlasmodium falciparumYield (engineering)CatalysisCombinatorial chemistryOxidative phosphorylationMalariaOrganic chemistryBiochemistryChromatographyMaterials scienceMetallurgyBiologyImmunologyQuinazolinone synthesis and applicationsPhenothiazines and Benzothiazines Synthesis and ActivitiesAdvanced Synthetic Organic Chemistry