Regioselective C3 Alkenylation of 4H-pyrido[1,2-a] pyrimidin-4-ones via Palladium-Catalyzed C-H Activation

被引：28

作者：

Liu, Wenjie ^{[1
]}

Wang, Shaohua ^{[1
]}

Zhang, Qi ^{[1
]}

Yu, Jingwen ^{[1
]}

Li, Jiahe ^{[1
]}

Xie, Zhiwei ^{[1
]}

Cao, Hua ^{[1
]}

机构：

[1] Guangdong Pharmaceut Univ, Sch Chem & Chem Engn, Guangzhou 510006, Guangdong, Peoples R China

来源：

CHEMISTRY-AN ASIAN JOURNAL | 2014年 / 9卷 / 09期

基金：

中国国家自然科学基金;

关键词：

alkenylation; C-H activation; homogeneous catalysis; palladium; regioselectivity; EFFLUX PUMP INHIBITORS; PALLADIUM(II)-CATALYZED DIRECT ALKENYLATION; DIRECT OXIDATIVE ALKENYLATION; PSEUDOMONAS-AERUGINOSA; DEHYDROGENATIVE ALKENYLATION; INTERMOLECULAR ALKENYLATION; BOND FUNCTIONALIZATION; DIRECT ARYLATION; INDOLES; OLEFINATION;

D O I：

10.1002/asia.201402455

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A general and efficient palladium-catalyzed direct C3 alkenylation of 4H-pyridoA1,2-a] pyrimidin-4-ones using AgOAc/O-2 as the oxidant has been developed. A variety of 4H-pyrido[1,2-a] pyrimidin-4-ones were successfully coupled with acrylate esters, styrenes, methylvinylketone, and acrylamide in moderate to excellent yields. The reaction exhibited complete regio-and stereoselectivity. This transformation provides an attractive new approach to functionalize 4HpyridoACHTUNGTRENUNG[ 1,2-a] pyrimidin-4-ones.

引用

页码：2436 / 2439

页数：4

共 76 条

[1]

[Anonymous], 2012, ANGEW CHEM

[2] Palladium-Catalyzed Dehydrogenative Coupling of Furans with Styrenes [J].

Aouf, Chahinez ;

Thiery, Emilie ;

Le Bras, Jean ;

Muzart, Jacques .

ORGANIC LETTERS, 2009, 11 (18) :4096-4099

[3] Mild aerobic oxidative palladium (II) catalyzed C-H bond functionalization: Regioselective and switchable C-H alkenylation and annulation of pyrroles [J].

Beck, EM ;

Grimster, NP ;

Hatley, R ;

Gaunt, MJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (08) :2528-2529

[4] Overcoming the "Oxidant Problem": Strategies to Use O2 as the Oxidant in Organometallic C-H Oxidation Reactions Catalyzed by Pd (and Cu) [J].

Campbell, Alison N. ;

Stahl, Shannon S. .

ACCOUNTS OF CHEMICAL RESEARCH, 2012, 45 (06) :851-863

[5] Highly regioselective C-H bond functionalization: palladium-catalyzed arylation of substituted imidazo[1,2-a]pyridine with aryl chlorides [J].

Cao, Hua ;

Lin, Yuanguang ;

Zhan, Haiying ;

Du, Zuodong ;

Lin, Xiulian ;

Liang, Qi-Mei ;

Zhang, Hong .

RSC ADVANCES, 2012, 2 (14) :5972-5975

[6] Direct Arylation of Imidazo[1,2-a]pyridine at C-3 with Aryl Iodides, Bromides, and Triflates via Copper(I)-Catalyzed C-H Bond Functionalization [J].

Cao, Hua ;

Zhan, Haiying ;

Lin, Yuanguang ;

Lin, Xiulian ;

Du, Zuodong ;

Jiang, Huanfeng .

ORGANIC LETTERS, 2012, 14 (07) :1688-1691

[7] Palladium-Catalyzed Direct Arylation Reaction of 2,3,5-Trisubstituted Furans with Aryl Iodides or Aryl Bromides [J].

Cao, Hua ;

Shen, Dongsheng ;

Zhan, Haiying ;

Yang, Liuqing .

SYNLETT, 2011, (10) :1472-1476

[8] Directed palladation: fine tuning permits the catalytic 2-alkenylation of indoles [J].

Capito, E ;

Brown, JM ;

Ricci, A .

CHEMICAL COMMUNICATIONS, 2005, (14) :1854-1856

[9] SYNTHESIS OF 4(1H)-QUINOLONES BY THERMOLYSIS OF ARYLAMINOMETHYLENE MELDRUM ACID-DERIVATIVES [J].

CASSIS, R ;

TAPIA, R ;

VALDERRAMA, JA .

SYNTHETIC COMMUNICATIONS, 1985, 15 (02) :125-133

[10] Palladium-catalyzed ortho-alkenylation of aryl hydrogen phosphates using a new mono-phosphoric acid directing group [J].

Chan, Li Yan ;

Kim, Sunggak ;

Ryu, Taekyu ;

Lee, Phil Ho .

CHEMICAL COMMUNICATIONS, 2013, 49 (41) :4682-4684

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