Commercial Copper‐Catalyzed Aerobic Oxidative Synthesis of 4H‐3,1‐Benzoxazine and Their Effects on Anti‐Inflammatory Genes Expression

Abstract

A facile green synthesis of the anti‐inflammatory gene expression of 4H‐3,1‐benzoxazine was developed under a commercial copper catalytic system. Benzoxazines were synthesized from 2‐aminobenzyl alcohols and aromatic aldehydes including heterocyclic aromatic aldehydes using an economical commercially available copper(I)iodide (CuI) as a catalyst in the presence of the base, ^tBuOK. Target products were achieved in moderate to high yields with up to 75 % isolated yield. 4H‐3,1‐Benzoxazine enabled down‐regulation of inflammatory gene expression including tumor necrosis factor‐α (TNF‐α), inducible nitric oxide synthase (iNOS), cyclooxygenase‐2 (COX‐2), and interleukin‐1β (IL‐1β) in the lipopolysaccharide (LPS)‐stimulated RAW 264.7 macrophage cell line using a real‐time quantitative polymerase chain reaction (RT‐qPCR) comparable to anti‐inflammatory drug, dexamethasone. These results demonstrated that 4H‐3,1‐Benzoxazines possess the potential capability of anti‐inflammation.