Cu-catalyzed one-pot synthesis of fused oxazepinone derivatives via sp2 C-H and O-H cross-dehydrogenative coupling

被引：11

作者：

Zhang, Zeyuan ^{[1
]}

Dai, Zhen ^{[1
]}

Ma, Xinkun ^{[1
]}

Liu, Yihan ^{[1
]}

Ma, Xiaojun ^{[1
]}

Li, Wanli ^{[1
]}

Ma, Chen ^{[1
,2
]}

机构：

[1] Shandong Univ, Sch Chem & Chem Engn, Jinan 250100, Peoples R China

[2] Peking Univ, State Key Lab Nat & Biomimet Drugs, Beijing 100191, Peoples R China

来源：

ORGANIC CHEMISTRY FRONTIERS | 2016年 / 3卷 / 07期

基金：

美国国家科学基金会;

关键词：

REMOVABLE BIDENTATE AUXILIARY; HIV-1; REVERSE-TRANSCRIPTASE; METHYLENE C(SP(3))-H BONDS; BENZOIC-ACID DERIVATIVES; CARBON-HYDROGEN BONDS; UGI-SMILES COUPLINGS; C(SP(2))-H BONDS; DIRECTING GROUP; PHARMACOLOGICAL EVALUATION; AMINOQUINOLINE BENZAMIDES;

D O I：

10.1039/c6qo00040a

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient Cu-catalyzed cascade reaction protocol was developed for the synthesis of fused oxazepinone derivatives via sp(2) C-H and O-H cross-dehydrogenative coupling. A readily available catalyst, Cu2O, was used in this modular and convergent approach. An unusual Smiles rearrangement reaction was involved in this synthesis. Various reaction parameters were evaluated and optimized, and the target compounds were obtained in good-to-excellent yields.

引用

页码：799 / 803

页数：5

共 78 条

[1] Rational Design and Synthesis of Potent Dibenzazepine Motifs as β-Secretase Inhibitors [J].

Al-Tel, Taleb H. ;

Al-Qawasmeh, Raed A. ;

Schmidt, Marco F. ;

Al-Aboudi, Amal ;

Rao, Shashidhar N. ;

Sabri, Salim S. ;

Voelter, Wolfgang .

JOURNAL OF MEDICINAL CHEMISTRY, 2009, 52 (20) :6484-6488

[2] An unusual radical smiles rearrangement [J].

Bacqué, E ;

El Qacemi, M ;

Zard, SZ .

ORGANIC LETTERS, 2005, 7 (17) :3817-3820

[3] Four-Component Synthesis of Imidazolinium-Fused Heterocycles from Ugi-Smiles Couplings [J].

Barthelon, Anaelle ;

Legoff, Xavier-Frederic ;

El Kaim, Laurent ;

Grimaud, Laurence .

SYNLETT, 2010, (01) :153-157

[4] Thiols in Ugi- and Passerini-Smiles-Type Couplings [J].

Barthelon, Anaelle ;

El Kaim, Laurent ;

Gizolme, Marie ;

Grimaud, Laurence .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2008, 2008 (35) :5974-5987

[5] A DIRECT SYNTHESIS OF OLEFINS BY REACTION OF CARBONYL-COMPOUNDS WITH LITHIO DERIVATIVES OF 2-[ALKYL-SULFONYL OR (2'-ALKENYL)-SULFONYL OR BENZYL-SULFONYL]-BENZOTHIAZOLES [J].

BAUDIN, JB ;

HAREAU, G ;

JULIA, SA ;

RUEL, O .

TETRAHEDRON LETTERS, 1991, 32 (09) :1175-1178

[6] Antiproliferative and Differentiating Activities of a Novel Series of Histone Deacetylase Inhibitors [J].

Binaschi, Monica ;

Boldetti, Andrea ;

Gianni, Maurizio ;

Maggi, Carlo Alberto ;

Gensini, Martina ;

Bigioni, Mario ;

Parlani, Massimo ;

Giolitti, Alessandro ;

Fratelli, Maddalena ;

Valli, Claudia ;

Terao, Mineko ;

Garattini, Enrico .

ACS MEDICINAL CHEMISTRY LETTERS, 2010, 1 (08) :411-415

[7] Cu(II)-Mediated C-S/N-S Bond Formation via C-H Activation: Access to Benzoisothiazolones Using Elemental Sulfur [J].

Chen, Fa-Jie ;

Liao, Gang ;

Li, Xin ;

Wu, Jun ;

Shi, Bing-Feng .

ORGANIC LETTERS, 2014, 16 (21) :5644-5647

[8] Pd(II)-catalyzed alkoxylation of unactivated C(sp3)-H and C(sp2)-H bonds using a removable directing group: efficient synthesis of alkyl ethers [J].

Chen, Fa-Jie ;

Zhao, Sheng ;

Hu, Fang ;

Chen, Kai ;

Zhang, Qi ;

Zhang, Shuo-Qing ;

Shi, Bing-Feng .

CHEMICAL SCIENCE, 2013, 4 (11) :4187-4192

[9] Palladium-catalyzed C(sp3)-H arylation of lactic acid: efficient synthesis of chiral β-aryl-α-hydroxy acids [J].

Chen, Kai ;

Li, Xin ;

Zhang, Shuo-Qing ;

Shi, Bing-Feng .

ORGANIC CHEMISTRY FRONTIERS, 2016, 3 (02) :204-208

[10] Synthesis of chiral α-hydroxy acids via palladium-catalyzed C(sp3)-H alkylation of lactic acid [J].

Chen, Kai ;

Li, Xin ;

Zhang, Shuo-Qing ;

Shi, Bing-Feng .

CHEMICAL COMMUNICATIONS, 2016, 52 (09) :1915-1918

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