Unique regioselective C-H diacetoxylation of pyrrolo[2,3-d]pyrimidine derivatives promoted by sodium iodide

被引：5

作者：

Mao, Zhengtong ^{[1
]}

Jiang, Yunfeng ^{[1
]}

Liu, Min ^{[1
]}

Zhang, Xingxian ^{[1
]}

机构：

[1] Zhejiang Univ Technol, Coll Pharmaceut Sci, Hangzhou 310014, Zhejiang, Peoples R China

来源：

TETRAHEDRON LETTERS | 2021年 / 84卷

基金：

中国国家自然科学基金;

关键词：

Diacetoxylation; Unique regioselectivity; Palladium-catalyzed; Sodium iodide; Pyrrolo[2; 3-d]pyrimidine; ORTHO-ALKOXYLATION; BOND; ACETOXYLATION; ACYLOXYLATION; 7-DEAZAPURINE; OXYGENATION; ARENES;

D O I：

10.1016/j.tetlet.2021.153435

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The palladium-catalyzed direct C-H diacetoxylation of pyrrolo[2,3-d]pyrimidine derivatives was realized in a mild, efficient and high regioselective manner. The amounts of sodium iodide is a critical factor for the unique regioselectivity of this catalytic system. A wide range of functional groups are tolerated in this protocol, which can be further modified and potentially of great importance in medicinal chemistry. (c) 2021 Published by Elsevier Ltd.

引用

页数：5

共 32 条

[1] Carboxylate-Assisted Ruthenium-Catalyzed Alkyne Annulations by C-H/Het-H Bond Functionalizations [J].

Ackermann, Lutz .

ACCOUNTS OF CHEMICAL RESEARCH, 2014, 47 (02) :281-295

[2] Copper-Catalyzed Dehydrogenative Coupling of Arenes with Alcohols [J].

Bhadra, Sukalyan ;

Matheis, Christian ;

Katayev, Dmitry ;

Goossen, Lukas J. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (35) :9279-9283

[3] Purinyl N1-Directed Aromatic C-H Oxidation in 6-Arylpurines and 6-Arylpurine Nucleosides [J].

Chamala, Raghu Ram ;

Parrish, Damon ;

Pradhan, Padmanava ;

Lakshman, Mahesh K. .

JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (15) :7423-7435

[4] Synthetic Entries to and Biological Activity of Pyrrolopyrimidines [J].

De Coen, Laurens M. ;

Heugebaert, Thomas S. A. ;

Garcia, Daniel ;

Stevens, Christian V. .

CHEMICAL REVIEWS, 2016, 116 (01) :80-139

[5] Palladium-catalyzed oxygenation of unactivated sp3 C-H bonds [J].

Desai, LV ;

Hull, KL ;

Sanford, MS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (31) :9542-9543

[6] A highly selective catalytic method for the oxidative functionalization of C-H bonds [J].

Dick, AR ;

Hull, KL ;

Sanford, MS .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (08) :2300-2301

[7] Palladium-catalyzed C-H bond functionalization/oxidative acyloxylation of 2-aryl-benzo[d]thiazoles [J].

Ding, Qiuping ;

Ji, Huafang ;

Nie, Ziyi ;

Yang, Qin ;

Peng, Yiyuan .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2013, 739 :33-39

[8] Novel synthesis and antifungal activity of pyrrole and pyrrolo[2,3-d]pyrimidine derivatives containing sulfonamido moieties [J].

El-Gaby, MSA ;

Gaber, AM ;

Atalla, AA ;

Al-Wahab, KAA .

FARMACO, 2002, 57 (08) :613-617

[9] Nature-inspired pyrrolo[2,3-d]pyrimidines targeting the histamine H3 receptor [J].

Frank, Annika ;

Meza-Arriagada, Francisco ;

Salas, Cristian O. ;

Espinosa-Bustos, Christian ;

Stark, Holger .

BIOORGANIC & MEDICINAL CHEMISTRY, 2019, 27 (14) :3194-3200

[10] Highly Selective Palladium-Catalyzed Arene C-H Acyloxylation with Benzothiadiazole as a Modifiable Directing Group [J].

Guo, Jie ;

He, Hui ;

Ye, Zenghui ;

Zhu, Kai ;

Wu, Yanqi ;

Zhang, Fengzhi .

ORGANIC LETTERS, 2018, 20 (18) :5692-5695

← 1 2 3 4 →