Synthesis of Spirofurooxindoles via Phenyliodine(III) Bis(trifluoroacetate) (PIFA)-Mediated Cascade Oxidative C-O and C-C Bond Formation

被引：22

作者：

Sun, Desong ^{[1
]}

Zhao, Xiaoyuan ^{[1
]}

Zhang, Bobo ^{[1
]}

Cong, Ying ^{[1
]}

Wan, Xintong ^{[1
]}

Bao, Mingmai ^{[1
]}

Zhao, Xue ^{[1
]}

Li, Bing ^{[1
]}

Zhang-Negrerie, Daisy ^{[1
]}

Du, Yunfei ^{[1
,2
]}

机构：

[1] Tianjin Univ, Sch Pharmaceut Sci & Technol, Tianjin Key Lab Modern Drug Delivery & High Effic, Tianjin 300072, Peoples R China

[2] Collaborat Innovat Ctr Chem Sci & Engn Tianjin, Tianjin 300072, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2018年 / 360卷 / 08期

基金：

中国国家自然科学基金;

关键词：

spirofurooxindole; cascade reaction; hypervalent iodine oxidant; metal-free conditions; spirocyclization; N-HETEROCYCLIC CARBENE; SPIRO GAMMA-BUTYROLACTONES; HYPERVALENT IODINE; STEREOSELECTIVE-SYNTHESIS; SPIROOXINDOLE LACTONES; 3+2 ANNULATION; DERIVATIVES; ACID; CYCLIZATION; ISATINS;

D O I：

10.1002/adsc.201701635

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Upon treatment with solely a hypervalent iodine reagent of phenyliodine(III) bis(tri-fluoroacetate) (PIFA), 3-(2-hydroxyphenyl)-3-oxo-N-phenyl propanamides and a series of its derivatives were conveniently converted to a class of undocumented spirofurooxindoles under mild conditions. Control experiments provided evidence that this spirocyclization process encompassed a cascade oxidative reactions involving the formation of a C-O bond prior to that of C-C bond.

引用

页码：1634 / 1638

页数：5

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