Metal-Free Synthesis of 3-Arylquinolin-2-ones from N,2-Diarylacrylamides via Phenyliodine(III) Bis(2,2-dimethylpropanoate)-Mediated Direct Oxidative C-C Bond Formation

被引：11

作者：

Cao, Yang ^{[1
]}

Zhao, Hui ^{[2
]}

Zhang-Negrerie, Daisy ^{[1
]}

Du, Yunfei ^{[1
]}

Zhao, Kang ^{[1
]}

机构：

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

[2] Shandong Agr Univ, Coll Chem & Mat Sci, Taian City 271018, Shandong, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2016年 / 358卷 / 22期

基金：

美国国家科学基金会;

关键词：

3-arylquinolin-2-ones; C(sp(2))-C(sp(2)) bond formation; organoiodine(III) compounds; oxidative annulation; HIV-1; REVERSE-TRANSCRIPTASE; CHAGAS-DISEASE; CANCER DRUG; DERIVATIVES; ALKENES; QUINOLINONES; INHIBITORS; CYCLIZATION; ACTIVATION; ALKALOIDS;

D O I：

10.1002/adsc.201600512

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Treatment of N,2-diarylacrylamides with the organoiodine(III) compound phenyliodine(III) bis(2,2-dimethylpropanoate) [PhI(O2C-t-Bu)(2)] and boron trifluoride etherate (BF3 center dot Et2O) resulted in a direct and selective oxidative C(sp(2))-C(sp(2)) bond formation leading to a convenient assemblage, under mild conditions, of the biologically important 3-arylquinolin-2-one skeleton. Differing from the five-membered oxindole products from oxidative cyclizations mediated by transition metals, this metal-free approach realized a direct annulation of the N-arylacrylamide into a six-membered 3-arylquinolin-2-one skeleton.

引用

页码：3610 / 3615

页数：6

共 44 条

[1]

ALONSO MA, 1993, HETEROCYCLES, V36, P2315

[2]

[Anonymous], 2013, ANGEW CHEM INT ED, V52, P3972

[3]

[Anonymous], 2013, ANGEW CHEM INT ED, V52, P7156

[4] Novel lactonization with phenonium ion participation induced by hypervalent iodine reagents [J].