One-pot, two-step synthesis and photophysical properties of 2-(5-phenylindol-3-yl) benzimidazole derivatives

被引:18
作者
Lyu, Liu [1 ]
Cai, Liu [1 ]
Wang, Yun [2 ]
Huang, Jinfeng [1 ]
Zeng, Xiangchao [1 ]
Liu, Porun [2 ]
机构
[1] Jinan Univ, Coll Chem & Mat Sci, Guangzhou 510632, Guangdong, Peoples R China
[2] Griffith Univ, Ctr Clean Environm & Energy, Gold Coast Campus, Southport, Qld 4222, Australia
关键词
HOLE TRANSPORT MATERIALS; BIOLOGICAL EVALUATION; FLUORESCENT SENSOR; FLUORIDE-ION; IN-VITRO; EFFICIENT; DESIGN; CHEMOSENSOR; INHIBITION; AGENTS;
D O I
10.1039/c7ra09864b
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An efficient one-pot, two-step procedure has been successfully applied for the synthesis of a series of 2-(5-phenylindol- 3-yl) benzimidazoles. The first step was cyclocondensation-oxidation of 5-bromoindole-3-aldehydes with o-phenylenediamines in 1,4-dioxane, which was promoted by activated carbon and used atmospheric air as a "green" oxidant. The resulting 2-(5-bromoindol-3-yl) benzimidazoles in the pot were in situ coupled with postadded phenylboronic acids, and catalyzed with PdCl2(dppf) in 1,4-dioxane-H2O to afford the desired compounds with satisfactorily high yields. The relationship between the synthesized compounds' absorption, and fluorescence spectra with molecular structures has been investigated with experimental data and theoretical calculations.
引用
收藏
页码:49374 / 49385
页数:12
相关论文
共 50 条
[41]   SYNTHESIS AND EVALUATION OF BIOLOGICAL PROPERTIES OF 2-(2-(PHENOXY)PYRIDIN-3-YL)QUINAZOLIN-4(3H)-ONE DERIVATIVES [J].
Zhang, Li-qiong ;
Liu, Jia-min ;
Gan, Yi-yuan ;
Shao, Li-hui ;
Fu, Yi-hong ;
Wang, Zhen-chao ;
Ouyang, Gui-ping .
HETEROCYCLES, 2020, 100 (11) :1845-1858
[42]   Facile synthesis of 2,3-benzodiazepines using one-pot two-step phosphate-assisted acylation-hydrazine cyclization reactions [J].
Sumita, Akinari ;
Lee, Jinhee ;
Otani, Yuko ;
Ohwada, Tomohiko .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (21) :4013-4020
[43]   One-pot two-step catalytic synthesis of 6-amino-2-pyridone-3,5-dicarbonitriles enabling anti-cancer bioactivity [J].
Nicely, Lynden G. ;
Vala, Ruturajsinh M. ;
Upadhyay, Dipti B. ;
Nogales, Joaquina ;
Chi, Celestine ;
Banerjee, Sourav ;
Patel, Hitendra M. .
RSC ADVANCES, 2022, 12 (37) :23889-23897
[44]   A consecutive one-pot two-step approach to trifluoromethylated pyrazolo [4′,3′:5,6]pyrano[2,3-b]indoles promoted by molecular iodine [J].
Zhu, Yingjun ;
Chen, Fanhui ;
Zhou, Yidi ;
Kang, Zhangping ;
Zhang, Min ;
Deng, Hongmei ;
Song, Liping .
JOURNAL OF FLUORINE CHEMISTRY, 2018, 211 :141-147
[45]   Microwave-assisted one-pot multicomponent synthesis of 2-(-4-oxo-2-(1-(2-oxo-2h-chromen-3-yl) ethylidene)hydrazono)thiazolidin-5-yl) acetic acid derivatives and their antiviral activity [J].
Varluvothu, Anjaneyulu ;
Vaarla, Krishnaiah ;
Vermeire, Kurt ;
Leelavathi, Panaganti .
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2022, 59 (09) :1604-1615
[46]   Efficient One-Pot Multicomponent Synthesis of (Carbazolylamino)furan-2(5H)-one and Carbazolyltetrahydropyrimidine Derivatives [J].
Ramesh, Subburethinam ;
Nagarajan, Rajagopal .
SYNTHESIS-STUTTGART, 2011, (20) :3307-3317
[47]   One-Pot Two-Component [3+2] Cycloaddition/Annulation Protocol for the Synthesis of Highly Functionalized Thiophene Derivatives [J].
Nandi, Ganesh Chandra ;
Samai, Subhasis ;
Singh, Maya Shankar .
JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (19) :8009-8014
[48]   A novel annulation reaction of N-substituted-2-nitrosoanilines with esters of α-isocyano acids. A one-pot, two-step route to 2-benzimidazole-substituted esters of α-amino acids [J].
Bujok, Robert ;
Cmoch, Piotr ;
Wrobel, Zbigniew .
TETRAHEDRON LETTERS, 2014, 55 (23) :3410-3413
[49]   One-Pot, Two-Step Synthesis of Imidazo[1,2-a]benzimidazoles via A Multicomponent [4+1] Cycloaddition Reaction [J].
Hsiao, Ya-Shan ;
Narhe, Bharat D. ;
Chang, Ying-Sheng ;
Sun, Chung-Ming .
ACS COMBINATORIAL SCIENCE, 2013, 15 (10) :551-555
[50]   One-Pot, Two-Step Protocol for the Catalytic Asymmetric Synthesis of Optically Active N,O- and O,O-Acetals [J].
Polat, M. Fatih ;
Hettmanczyk, Lara ;
Zhang, Wei ;
Szabo, Zoltan ;
Franzen, Johan .
CHEMCATCHEM, 2013, 5 (06) :1334-1339