Method for the Synthesis of 2 H-1,4-Benzoxazin-3-(4 H )-ones via Ligand-Free Copper-Catalyzed Cascade Reaction

被引：3

作者：

Zhang, Lingyu ^{[1
]}

Zhang, Songlin ^{[1
]}

机构：

[1] Soochow Univ, Coll Chem Chem Engn & Mat Sci, Key Lab Organ Synth Jiangsu Prov, Suzhou 215123, Peoples R China

来源：

SYNTHESIS-STUTTGART | 2023年 / 55卷 / 19期

基金：

中国国家自然科学基金;

关键词：

copper; cross-coupling; ligand-free; Ullmann reaction; 2; H-1; 4-benzoxazin-3-(4 H )-ones; ONE-POT SYNTHESIS; CROSS-COUPLING REACTIONS; O-HALOPHENOLS; ARYL HALIDES; DERIVATIVES; 2H-1,4-BENZOXAZIN-3-(4H)-ONES; BENZOXAZINES; ARYLAMINES; INHIBITORS; ARYLATION;

D O I：

10.1055/a-2110-1989

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient method for the synthesis of 2H-1,4-benzoxaz-in-3-(4H)-ones via ligand-free copper-catalyzed cascade reaction of substituted chloroacetamides with 2-halophenols has been developed for the first time. Some of the issues typically encountered during the synthesis of 2H-1,4-benzoxazin-3-(4H)-ones, including adding noble metals and ligands, poor substrate scope, have been addressed using this newly developed ligand-free copper-catalyzed cascade reaction.

引用

页码：3179 / 3185

页数：7

共 56 条

[1] Identification and Development of an Efficient Route to SB-649915 [J].

Armitage, Mark ;

Bret, Guillaume ;

Choudary, Bernie M. ;

Kingswood, Mike ;

Loft, Mike ;

Moore, Steve ;

Smith, Steve ;

Urquhart, Michael W. J. .

ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2012, 16 (10) :1626-1634

[2] Synthesis of functionalised pyrido[4,3-b][1,4]oxazine and imidazo[1,2-a]pyridine derivatives [J].

Arrault, A ;

Touzeau, F ;

Guillaumet, G ;

Léger, JM ;

Jarry, C ;

Mérour, JY .

TETRAHEDRON, 2002, 58 (40) :8145-8152

[3] Recent Advances in Microwave-Assisted Copper-Catalyzed Cross-Coupling Reactions [J].

Baqi, Younis .

CATALYSTS, 2021, 11 (01) :1-35

[4] N6-[(Hetero)aryl/(cyclo)alkyl-carbamoyi-methoxy-phenyl]-(2chloro)-5′-N-ethylearboxamido-adenosines:: The first example of adenosine-related structures with potent agonist activity at the human A2B adenosine receptor [J].

Baraldi, Pier Giovanni ;

Preti, Delia ;

Tabrizi, Mojgan Aghazadeh ;

Fruttarolo, Francesca ;

Saponaroa, Giulia ;

Baraldi, Stefania ;

Romagnoli, Romeo ;

Moorman, Allan R. ;

Gessi, Stefania ;

Varani, Katia ;

Borea, Pier Andrea .

BIOORGANIC & MEDICINAL CHEMISTRY, 2007, 15 (07) :2514-2527

[5] Copper in cross-coupling reactions - The post-Ullmann chemistry [J].

Beletskaya, IP ;

Cheprakov, AV .

COORDINATION CHEMISTRY REVIEWS, 2004, 248 (21-24) :2337-2364

[6] Nickel-Catalyzed Cascade Reactions [J].

Bhakta, Sayantika ;

Ghosh, Tapas .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2021, 2021 (29) :4201-4215

[7] Selected Copper-Based Reactions for C-N, C-O, C-S, and C-C Bond Formation [J].

Bhunia, Subhajit ;

Pawar, Govind Goroba ;

Kumar, S. Vijay ;

Jiang, Yongwen ;

Ma, Dawei .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (51) :16136-16179

[8] Synthesis by microwave irradiation of a substituted benzoxazine parallel library with preferential relaxant activity for guinea pig trachealis [J].

Caliendo, G ;

Perissutti, E ;

Santagada, V ;

Fiorino, F ;

Severino, B ;

Cirillo, D ;

Bianca, RDD ;

Lippolis, L ;

Pinto, A ;

Sorrentino, R .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2004, 39 (10) :815-826

[9] Synthesis, biological activity and conformational study of 1,4-benzoxazine derivatives as potassium channel modulators [J].

Caliendo, G ;

Grieco, P ;

Perissutti, E ;

Santagada, V ;

Santini, A ;

Albrizio, S ;

Fattorusso, C ;

Pinto, A ;

Sorrentino, R .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1998, 33 (12) :957-967

[10] Discovery of new small molecule inhibitors targeting isocitrate dehydrogenase 1 (IDH1) with blood-brain barrier penetration [J].

Cao, Hengyi ;

Zhu, Guangya ;

Sun, Lin ;

Chen, Ge ;

Ma, Xinxin ;

Luo, Xiao ;

Zhu, Jidong .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2019, 183

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