Rhodium-Catalyzed Direct and Selective ortho C-H Chalcogenation of N-(Hetero)aryl-7-azaindoles

被引：40

作者：

Vats, Tripta Kumari ^{[1
]}

Mishra, Aniket ^{[1
]}

Deb, Indubhusan ^{[1
]}

机构：

[1] CSIR Indian Inst Chem Biol, Organ & Med Chem Div, 4 Raja SC Mullick Rd, Kolkata 700032, India

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2018年 / 360卷 / 12期

关键词：

C-H bond activation; 7-azaindoles; 7-azaindolines; sulfur; selenium; rhodium; BOND FORMATION; DIRECT THIOLATION; SULFURATING REAGENT; ANTITUMOR-ACTIVITY; EFFICIENT ACCESS; ALIPHATIC AMIDES; C(SP(3))-H BONDS; ROOM-TEMPERATURE; 7-AZAINDOLES; ARENES;

D O I：

10.1002/adsc.201800090

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

Rhodium catalyzed synthesis of chalcogenated N-aryl-7-azaindoles/azaindolines has been developed through N-directed ortho Csp(2)-H activation in presence of silver triflate and silver carbonate in 1,4-dioxane using dichalcogenides. We have established this methodology as being efficient, highly regioselective and scalable, having a broad substrates scope. Through this route, a range of substrates have furnished thiolation and selenylation of azaindoles and azaindolines in good to excellent yields. These molecules could have potential application in biological and/or material science.

引用

页码：2291 / 2296

页数：6

共 72 条

[1]

Barun B. V., 2014, J ORG CHEM, V79, P9655

[2] Transition-Metal-Catalyzed C-S, C-Se, and C-Te Bond Formation via Cross-Coupling and Atom-Economic Addition Reactions [J].

Beletskaya, Irina P. ;

Ananikov, Valentine P. .

CHEMICAL REVIEWS, 2011, 111 (03) :1596-1636

[3] Selenium nanomaterials: An overview of recent developments in synthesis, properties and potential applications [J].

Chaudhary, Savita ;

Umar, Ahmad ;

Mehta, S. K. .

PROGRESS IN MATERIALS SCIENCE, 2016, 83 :270-329

[4] Cu(II)-catalyzed functionalizations of aryl C-H bonds using O2 as an oxidant [J].

Chen, Xiao ;

Hao, Xue-Shi ;

Goodhue, Charles E. ;

Yu, Jin-Quan .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (21) :6790-6791

[5] Cu(II)-Mediated Methylthiolation of Aryl C-H Bonds with DMSO [J].

Chu, Lingling ;

Yue, Xuyi ;

Qing, Feng-Ling .

ORGANIC LETTERS, 2010, 12 (07) :1644-1647

[6] COMPARISON OF RANITIDINE AND CIMETIDINE IN THE TREATMENT OF GASTRIC HYPERSECRETION [J].

COLLEN, MJ ;

HOWARD, JM ;

MCARTHUR, KE ;

RAUFMAN, JP ;

CORNELIUS, MJ ;

CIARLEGLIO, CA ;

GARDNER, JD ;

JENSEN, RT .

ANNALS OF INTERNAL MEDICINE, 1984, 100 (01) :52-58

[7] Synthesis of polyheterocyclic nitrogen-containing marine natural products [J].

Fernández, D ;

Ahaidar, A ;

Danelón, G ;

Cironi, P ;

Marfil, M ;

Pérez, O ;

Cuevas, C ;

Albericio, F ;

Joule, JA ;

Alvarez, M .

MONATSHEFTE FUR CHEMIE, 2004, 135 (06) :615-627

[8] Expedient C-H Chalcogenation of Indolines and Indoles by Positional-Selective Copper Catalysis [J].

Gandeepan, Parthasarathy ;

Koeller, Julian ;

Ackermann, Lutz .

ACS CATALYSIS, 2017, 7 (02) :1030-1034

[9] Design and synthesis of classical and nonclassical 6-arylthio-2,4-diamino-5-ethylpyrrolo[2,3-d]pyrimidines as antifolates [J].

Gangjee, Aleem ;

Zeng, Yibin ;

Talreja, Tina ;

McGuire, John J. ;

Kisliuk, Roy L. ;

Queener, Sherry F. .

JOURNAL OF MEDICINAL CHEMISTRY, 2007, 50 (13) :3046-3053

[10] Nickel-Catalyzed ortho-C-H Thiolation of N-Benzoyl α-Amino Acid Derivatives [J].

Gao, Feng ;

Zhu, Wei ;

Zhang, Dengyou ;

Li, Shuangjie ;

Wang, Jiang ;

Liu, Hong .

JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (19) :9122-9130

← 1 2 3 4 5 6 7 8 →