RhIII-Catalyzed Redox-Neutral C-H Activation of Pyrazolones: An Economical Approach for the Synthesis of N-Substituted Indoles

被引:56
作者
Fan, Zhoulong [1 ]
Song, Shanshan [2 ]
Li, Wei [3 ]
Geng, Kaijun [1 ]
Xu, Youjun [3 ]
Miao, Ze-Hong [2 ]
Zhang, Ao [1 ]
机构
[1] Chinese Acad Sci, SIMM, CAS Key Lab Receptor Res, Shanghai 201203, Peoples R China
[2] Chinese Acad Sci, SIMM, State Key Lab Drug Res, Shanghai 201203, Peoples R China
[3] Shenyang Pharmaceut Univ, Sch Pharmaceut Engn, Shenyang 110016, Peoples R China
关键词
OXIDIZING DIRECTING GROUP; INTERNAL ALKYNES; REGIOSELECTIVE SYNTHESIS; BOND FUNCTIONALIZATION; ISOQUINOLONE SYNTHESIS; OXIDATIVE ANNULATION; EFFICIENT SYNTHESIS; OXIME ESTERS; DERIVATIVES; OXIDANT;
D O I
10.1021/ol503404p
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new strategy is reported for the economical synthesis of indoles bearing an N-(3-aminobut-2-enoyl) substituent through RhIII-catalyzed redox-neutral C-H activation of pyrazolones and alkynes. This approach utilizes cheap substrates and mild reaction conditions to access a unique class of indoles via a N-N bond oxidative cleavage without loss of the N-terminus, therefore meeting all the atom/step/redox economy principles.
引用
收藏
页码:310 / 313
页数:4
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