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TBHP‐Mediated Oxidative Decarboxylative Cyclization in Water: Direct and Sustainable Access to Anti‐malarial Polycyclic Fused Quinazolinones and Rutaecarpine
Author(s) -
Chen Xingyu,
Xia Fei,
Zhao Yifan,
Ma Ji,
Ma Yue,
Zhang Dong,
Yang Lan,
Sun Peng
Publication year - 2020
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.202000154
Subject(s) - chemistry , rutaecarpine , plasmodium falciparum , yield (engineering) , catalysis , combinatorial chemistry , oxidative phosphorylation , malaria , organic chemistry , biochemistry , chromatography , materials science , metallurgy , immunology , biology
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.