Naphthoquinone-Directed C-H Annulation and Csp3-H Bond Cleavage: One-Pot Synthesis of Tetracyclic Naphthoxazoles

被引：29

作者：

Wang, Meining ^{[1
,2
]}

Zhang, Chi ^{[3
]}

Sun, Li-Ping ^{[3
]}

Ding, Chunyong ^{[1
,2
]}

Zhang, Ao ^{[1
,2
]}

机构：

[1] Chinese Acad Sci, Shanghai Inst Mat Med, CAS Key Lab Receptor Res, Shanghai 201203, Peoples R China

[2] Chinese Acad Sci, Shanghai Inst Mat Med, SOMCL, Shanghai 201203, Peoples R China

[3] China Pharmaceut Univ, Dept Med Chem, Nanjing 210009, Jiangsu, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2014年 / 79卷 / 10期

关键词：

OXIDATIVE ANNULATION; INTERNAL ALKYNES; DNA-BINDING; BENZOXAZOLES; ACTIVATION; FUNCTIONALIZATION; DERIVATIVES; COUPLING/CYCLIZATION; ISOQUINOLINES; STRATEGY;

D O I：

10.1021/jo500572u

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

One-pot synthesis of tetracyclic naphthoxazole derivatives from electron-deficient naphthoquinones and alkynes was achieved via Rh(III)-catalyzed C-H activation and C-sp3-H bond cleavage for the first time. This approach proceeds through a tandem cascade process involving substrate tautomerization, C-H activation, oxidative addition, cyclization, and aromatization. In addition, broad substrate scope, simple starting materials, and steric tolerance make this strategy of great practicality.

引用

页码：4553 / 4560

页数：8