Multicomponent cascade reaction: dual role of copper in the synthesis of 1,2,3-triazole tethered benzimidazo[1,2-a] quinoline and their photophysical studies

被引：13

作者：

Nagesh, Hunsur Nagendra ^{[1
]}

Suresh, Amaroju ^{[1
]}

Reddy, Muthyala Nagarjuna ^{[2
]}

Suresh, Narva ^{[1
]}

Subbalakshmi, Jayanty ^{[1
]}

Sekhar, Kondapalli Venkata Gowri Chandra ^{[1
]}

机构：

[1] Birla Inst Technol & Sci Pilani, Dept Chem, Hyderabad Campus, Hyderabad 500078, Telangana, India

[2] Univ Hyderabad, Sch Chem, Hyderabad 500046, Telangana, India

来源：

RSC ADVANCES | 2016年 / 6卷 / 19期

关键词：

CATALYZED N-ARYLATION; ONE-POT SYNTHESIS; ANTIPROLIFERATIVE ACTIVITY; BIOLOGICAL EVALUATION; ANTITUMOR EVALUATION; CRYSTAL-STRUCTURE; TANDEM SYNTHESIS; DNA-BINDING; IN-VITRO; DERIVATIVES;

D O I：

10.1039/c5ra24048d

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

One-pot synthesis of 1,2,3-triazole tethered benzimidazo[1,2-a] quinolines through a multi-component reaction is demonstrated. The domino/cascade reaction proceeds via click reaction, in which 1,2,3-triazole motif augment methylene group reactivity/N-C bond formation/Knoevenagel condensation in sequence. Overall one C-C bond and three C-N bonds are formed in a single step. In addition, photophysical properties of these new compounds were studied and compound 5u emerged as good fluorogenic substrate with quantum yield similar to 0.21.

引用

页码：15884 / 15894

页数：11

共 59 条

[1] Copper-catalyzed "click" reaction/direct arylation sequence: Modular syntheses of 1,2,3-triazoles
Ackermann, Lutz
Potukuchi, Harish K.
Landsberg, Dirk
Vicente, Ruben
[J]. ORGANIC LETTERS, 2008, 10 (14) : 3081 - 3084
[2] Click Chemistry: 1,2,3-Triazoles as Pharmacophores
Agalave, Sandip G.
Maujan, Suleman R.
Pore, Vandana S.
[J]. CHEMISTRY-AN ASIAN JOURNAL, 2011, 6 (10) : 2696 - 2718
[3] Antonio F. M., 2012, NEW J CHEM, V36, P1634
[4] Integration of the 1,2,3-Triazole "Click" Motif as a Potent Signalling Element in Metal Ion Responsive Fluorescent Probes
Ast, Sandra
Fischer, Tobias
Mueller, Holger
Mickler, Wulfhard
Schwichtenberg, Mathias
Rurack, Knut
Holdt, Hans-Juergen
[J]. CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (09) : 2990 - 3005
[5] Sequential synthesis of amino-1,4-naphthoquinone-appended triazoles and triazole-chromene hybrids and their antimycobacterial evaluation
Bala, Balasubramanian Devi
Muthusaravanan, Sivasubramanian
Choon, Tan Soo
Ali, Mohamed Ashraf
Perumal, Subbu
[J]. EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2014, 85 : 737 - 746
[6] Balme G, 2005, MULTICOMPONENT REACTIONS, P224, DOI 10.1002/3527605118.ch8
[7] One-Pot Synthesis of Triazolothiadiazepine 1,1-Dioxide Derivatives via Copper-Catalyzed Tandem [3+2] Cycloaddition/N-Arylation
Barange, Deepak Kumar
Tu, Yu-Chen
Kavala, Veerababurao
Kuo, Chun-Wei
Yao, Ching-Fa
[J]. ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (01) : 41 - 48
[8] Facile Synthesis of [1,2,3]-Triazole-Fused Isoindolines, Tetrahydroisoquinolines, Benzoazepines and Benzoazocines by Palladium-Copper Catalysed Heterocyclisation
Brahma, Kaushik
Achari, Basudeb
Chowdhury, Chinmay
[J]. SYNTHESIS-STUTTGART, 2013, 45 (04): : 545 - 555
[9] A CuAAC/Ullmann C-C Coupling Tandem Reaction: Copper-Catalyzed Reactions of Organic Azides with N-(2-Iodoaryl)propiolamides or 2-Iodo-N-(prop-2-ynyl)benzenamines
Cai, Qian
Yan, Jiajie
Ding, Ke
[J]. ORGANIC LETTERS, 2012, 14 (13) : 3332 - 3335
[10] Synthesis of Aza-Fused Polycyclic Quinolines through Copper-Catalyzed Cascade Reactions
Cai, Qian
Li, Zhengqiu
Wei, Jiajia
Fu, Liangbin
Ha, Chengyong
Pei, Duanqing
Ding, Ke
[J]. ORGANIC LETTERS, 2010, 12 (07) : 1500 - 1503

← 1 2 3 4 5 6 →