Copper-catalyzed one-pot synthesis of 1,4-benzothiazine-3-ones

被引：1

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：

TETRAHEDRON LETTERS | 2023年 / 130卷

基金：

中国国家自然科学基金;

关键词：

Copper catalyst; Cross-coupling; Nitrogen heterocycles; Ullmann reaction; 4-Benzothiazin-3-ones; C-N; DERIVATIVES; EFFICIENT; CHEMISTRY; BROMIDES;

D O I：

10.1016/j.tetlet.2023.154761

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient potassium carbonate and copper-mediated C-S and C-N Ullmann coupling reaction between 2-bromothiophenol and 2-haloacetanilide is reported here. This protocol affords a simple and efficient approach for the construction of 1,4-benzothiazinone-3-one derivatives, avoiding the limitations of using noble metals and expensive ligands for the first time.

引用

页数：4

共 37 条

[21] Novel Benzoxazine and Benzothiazine Derivatives as Multifunctional Antihyperlipidemic Agents [J].

Matralis, Alexios N. ;

Katselou, Maria G. ;

Nikitakis, Anastasios ;

Kourounakis, Angeliki P. .

JOURNAL OF MEDICINAL CHEMISTRY, 2011, 54 (15) :5583-5591

[22] Catalytic C-C, C-N, and C-O Ullmann-Type Coupling Reactions [J].

Monnier, Florian ;

Taillefer, Marc .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (38) :6954-6971

[23] MECHANISMS AND MODELS FOR COPPER MEDIATED NUCLEOPHILIC AROMATIC-SUBSTITUTION .2. A SINGLE CATALYTIC SPECIES FROM 3 DIFFERENT OXIDATION-STATES OF COPPER IN AN ULLMANN SYNTHESIS OF TRIARYLAMINES [J].

PAINE, AJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1987, 109 (05) :1496-1502

[24] Copper(I) Oxide/N,N-Bis[(2-furyl)methyl]oxalamide-Catalyzed Coupling of (Hetero)aryl Halides and Nitrogen Heterocycles at Low Catalytic Loading [J].

Pawar, Govind Goroba ;

Wu, Haibo ;

De, Subhadip ;

Ma, Dawei .

ADVANCED SYNTHESIS & CATALYSIS, 2017, 359 (10) :1631-1636

[25] One-Pot Tandem Access to Phenothiazine Derivatives from Acetanilide and 2-Bromothiophenol via Rhodium-Catalyzed C-H Thiolation and Copper-Catalyzed C-N Amination [J].

Rui, Xiyan ;

Wang, Chao ;

Si, Dongjuan ;

Hui, Xuechao ;

Li, Keting ;

Wen, Hongmei ;

Li, Wei ;

Liu, Jian .

JOURNAL OF ORGANIC CHEMISTRY, 2021, 86 (09) :6622-6632

[26] Copper catalysed Ullmann type chemistry: from mechanistic aspects to modern development [J].

Sambiagio, Carlo ;

Marsden, Stephen P. ;

Blacker, A. John ;

McGowan, Patrick C. .

CHEMICAL SOCIETY REVIEWS, 2014, 43 (10) :3525-3550

[27] Synergistic promoting effect of ball milling and KF-alumina support for the green synthesis of benzothiazinones [J].

Sharifi, Ali ;

Ansari, Mohammad ;

Darabi, Hossein Reza ;

Abaee, M. Saeed .

TETRAHEDRON LETTERS, 2016, 57 (05) :529-532

[28] Influence of glutathione on the oxidation chemistry of 5-S-cysteinyldopamine:: potentially neuroprotective reactions of relevance to Parkinson's disease [J].

Shen, XM ;

Dryhurst, G .

TETRAHEDRON, 2001, 57 (02) :393-405

[29]

SHIMIZU H, 1984, CHEM PHARM BULL, V32, P2571

[30] On a new formation-manner of diphenyl-amine-derivatives. [Preliminary announcement.] [J].

Ullmann, F .

BERICHTE DER DEUTSCHEN CHEMISCHEN GESELLSCHAFT, 1903, 36 :2382-2384

← 1 2 3 4 →