Rh(III)-catalyzed double molecular alkyne imine C-H activation: a facile and efficient synthesis of functionalized acridine compounds

被引：5

作者：

Shan, Yingying ^{[1
]}

Yan, Weidong ^{[1
]}

机构：

[1] Zhejiang Univ, Dept Chem, Hangzhou 310027, Zhejiang, Peoples R China

来源：

TETRAHEDRON LETTERS | 2016年 / 57卷 / 26期

关键词：

C-H activation; Acridine; Rh(III)-catalyzed; Alkyne imine; PROPARGYL-ALLENYL ISOMERIZATIONS; POLYFUNCTIONALIZED BENZENES; SEQUENTIAL REACTIONS; BOND ACTIVATION; DERIVATIVES; CONVENIENT; THIOPHENES; MECHANISM; PYRROLES; AZA;

D O I：

10.1016/j.tetlet.2016.05.077

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The construction of a new nitrogen heterocyclic ring via the C-H activation is a facile and efficient protocol to afford polysubstituted acridine compounds from simple, readily available starting materials. In this Letter, functionalized benzo[c]acridine and thieno[3,2-c]acridine compounds have been accomplished by the method of Rh(III)-catalyzed double molecular alkyne imine C-H activation. (C) 2016 Elsevier Ltd. All rights reserved.

引用

页码：2905 / 2909

页数：5

共 34 条

[1] Carboxylate-Assisted Ruthenium-Catalyzed Alkyne Annulations by C-H/Het-H Bond Functionalizations
Ackermann, Lutz
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 2014, 47 (02) : 281 - 295
[2] Carboxylate-Assisted Transition-Metal-Catalyzed C-H Bond Functionalizations: Mechanism and Scope
Ackermann, Lutz
[J]. CHEMICAL REVIEWS, 2011, 111 (03) : 1315 - 1345
[3] Ang L., 2006, ORG LETT, V8, P1233
[4] Research on potentially bioactive aza and thiaza polycyclic compounds containing a bridgehead nitrogen atom. III. Synthesis and antimicrobial activity of some 1,4-benzothiazines and pyrrolobenzothiazines
Armenise, D
Trapani, G
Arrivo, V
Laraspata, E
Morlacchi, F
[J]. JOURNAL OF HETEROCYCLIC CHEMISTRY, 2000, 37 (06) : 1611 - 1616
[5] C-H Bond Activation by f-Block Complexes
Arnold, Polly L.
McMullon, Max W.
Rieb, Julia
Kuehn, Fritz E.
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (01) : 82 - 100
[6] Recent Advances in the Synthesis of Indole and Quinoline Derivatives through Cascade Reactions
Barluenga, Jose
Rodriguez, Felix
Fananas, Francisco J.
[J]. CHEMISTRY-AN ASIAN JOURNAL, 2009, 4 (07) : 1036 - 1048
[7] Sulfone promoted Rh(III)-catalyzed C-H activation and base assisted 1,5-H shift strategy for the construction of seven-membered rings
Chen, Dianpeng
Xing, Gangdong
Zhou, Hongwei
[J]. ORGANIC CHEMISTRY FRONTIERS, 2015, 2 (08): : 947 - 950
[8] Weak Coordination as a Powerful Means for Developing Broadly Useful C-H Functionalization Reactions
Engle, Keary M.
Mei, Tian-Sheng
Wasa, Masayuki
Yu, Jin-Quan
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 2012, 45 (06) : 788 - 802
[9] Enantioselective iridium-catalyzed carbonyl allylation from the alcohol oxidation level via transfer hydrogenation: minimizing pre-activation for synthetic efficiency
Han, Soo Bong
Kim, In Su
Krische, Michael J.
[J]. CHEMICAL COMMUNICATIONS, 2009, (47) : 7278 - 7287
[10] Synthesis and mechanism of action studies of a series of norindenoisoquinoline topoisomerase I poisons reveal an inhibitor with a flipped orientation in the ternary DNA-enzyme-inhibitor complex as determined by X-ray crystallographic analysis
Ioanoviciu, A
Antony, S
Pommier, Y
Staker, BL
Stewart, L
Cushman, M
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 2005, 48 (15) : 4803 - 4814

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