Synthesis of Ring-Fused Oxazolo- and Pyrazoloisoquinolinones by a One-Pot Pd-Catalyzed Carboxamidation and Aldol-Type Condensation Cascade Process

被引:28
作者
Chouhan, Gagan [1 ]
Alper, Howard [1 ]
机构
[1] Univ Ottawa, Dept Chem, Ctr Catalysis Res & Innovat, Ottawa, ON K1N 6N5, Canada
基金
加拿大自然科学与工程研究理事会;
关键词
CARBONYLATIVE CYCLIZATION; MULTICOMPONENT SYNTHESIS; CYTOTOXIC ANTIBIOTICS; ORGANIC-SYNTHESIS; PALLADIUM; HETEROCYCLES; DERIVATIVES; ISOQUINOLINES; INHIBITORS; ANNULATION;
D O I
10.1021/jo9010574
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A three-component cascade process is described for the synthesis of ring-fused oxazolo- and pyrazoloisoquinolinones by a one-pot carboxamidation/aldol-type condensation reaction. The cascade process involves Pd-catalyzed carboxamidation of an aryl halide/active methylene compound with oxazolidinone or pyrazolidinone, and subsequent intramolecular base-catalyzed cyclization/dehydration through an aldol-type condensation process, to give ring-fused oxazolo- and pyrazoloisoquinolinones. This methodology provides an easy one-step approach to these important classes of nitrogen-containing heterocycles and can tolerate it wide array of functional groups, including ester, nitrile, methoxy, and halide.
引用
收藏
页码:6181 / 6189
页数:9
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