Convenient one-pot synthesis of 1,2,4-oxadiazoles and 2,4,6-triarylpyridines using graphene oxide (GO) as a metal-free catalyst: importance of dual catalytic activity

被引:10
作者
Basak, Puja [1 ]
Dey, Sourav [1 ]
Ghosh, Pranab [1 ]
机构
[1] Univ North Bengal, Dept Chem, Darjeeling, W Bengal, India
关键词
SOLVENT-FREE; EFFICIENT SYNTHESIS; GRAPHITE OXIDE; 3,5-DISUBSTITUTED 1,2,4-OXADIAZOLES; HYDROXYLAMINE HYDROCHLORIDE; ORGANIC-REACTIONS; ACID CATALYST; OXIDATION; CARBOCATALYSIS; ESTERIFICATION;
D O I
10.1039/d1ra06331f
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A convenient and efficient process for the synthesis of 3,5-disubstituted 1,2,4-oxadiazoles and 2,4,6-triarylpyridines has been described using an inexpensive, environmentally benign, metal-free heterogeneous carbocatalyst, graphene oxide (GO). GO plays a dual role of an oxidizing agent and solid acid catalyst for synthesizing 1,2,4-oxadiazoles and triarylpyridines. This dual catalytic activity of GO is due to the presence of oxygenated functional groups which are distributed on the nanosheets of graphene oxide. A broad scope of substrate applicability and good sustainability is offered in this developed protocol. The results of a few control experiments reveal a plausible mechanism and the role of GO as a catalyst was confirmed by FTIR, XRD, SEM, and HR-TEM analysis.
引用
收藏
页码:32106 / 32118
页数:13
相关论文
共 60 条
[1]   Microwave-assisted efficient, one-pot, three-component synthesis of 3,5-disubstituted 1,2,4-oxadiazoles under solvent-free conditions [J].
Adib, M ;
Jahromi, AH ;
Tavoosi, N ;
Mahdavi, M ;
Bijanzadeh, HR .
TETRAHEDRON LETTERS, 2006, 47 (17) :2965-2967
[2]   SYNTHETIC ANALOGS FOR THE STUDY OF GABA AS A NEUROTRANSMITTER [J].
ALLAN, RD ;
JOHNSTON, GAR .
MEDICINAL RESEARCH REVIEWS, 1983, 3 (02) :91-118
[3]   PTSA-ZnCl2: An Efficient Catalyst for the Synthesis of 1,2,4-Oxadiazoles from Amidoximes and Organic Nitriles [J].
Augustine, John Kallikat ;
Akabote, Vani ;
Hegde, Shrivatsa Ganapati ;
Alagarsamy, Padma .
JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (15) :5640-5643
[4]   Graphene oxide (GO) catalyzed transamidation of aliphatic amides: An efficient metal-free procedure [J].
Bhattacharya, Suchandra ;
Ghosh, Pranab ;
Basu, Basudeb .
TETRAHEDRON LETTERS, 2018, 59 (10) :899-903
[5]   Zinc(II)-Mediated Nitrile-Amidoxime Coupling Gives New Insights into H+-Assisted Generation of 1,2,4-Oxadiazoles [J].
Bolotin, Dmitrii S. ;
Kulish, Kirill I. ;
Bokach, Nadezhda A. ;
Starova, Galina L. ;
Gurzhiy, Vladislav V. ;
Kukushkin, Vadim Yu .
INORGANIC CHEMISTRY, 2014, 53 (19) :10312-10324
[6]   Structure and Cytotoxicity of Phidianidines A and B: First Finding of 1,2,4-Oxadiazole System in a Marine Natural Product [J].
Carbone, Marianna ;
Li, Yan ;
Irace, Carlo ;
Mollo, Ernesto ;
Castelluccio, Francesco ;
Di Pascale, Antonio ;
Cimino, Guido ;
Santamaria, Rita ;
Guo, Yue-Wei ;
Gavagnin, Margherita .
ORGANIC LETTERS, 2011, 13 (10) :2516-2519
[7]   3-ARYL-2-(3'-SUBSTITUTED-1',2',4'-OXADIAZOL-5'-YL)TROPANE ANALOGS OF COCAINE - AFFINITIES AT THE COCAINE BINDING-SITE AT THE DOPAMINE, SEROTONIN, AND NOREPINEPHRINE TRANSPORTERS [J].
CARROLL, FI ;
GRAY, JL ;
ABRAHAM, P ;
KUZEMKO, MA ;
LEWIN, AH ;
BOJA, JW ;
KUHAR, MJ .
JOURNAL OF MEDICINAL CHEMISTRY, 1993, 36 (20) :2886-2890
[8]   Metal-Free, Acid-Promoted Synthesis of Imidazole Derivatives via a Multicomponent Reaction [J].
Chen, Chung-Yu ;
Hu, Wan-Ping ;
Yan, Pi-Cheng ;
Senadi, Gopal Chandru ;
Wang, Jeh-Jeng .
ORGANIC LETTERS, 2013, 15 (24) :6116-6119
[9]   Graphene Oxide: An Efficient Acid Catalyst for the Construction of Esters from Acids and Alcohols [J].
Chen, Zhengwang ;
Wen, Yuelu ;
Fu, Yejuan ;
Chen, Hai ;
Ye, Min ;
Luo, Guotian .
SYNLETT, 2017, 28 (08) :981-985
[10]   Excellent catalytic performance of graphite oxide in the selective oxidation of glutaraldehyde by aqueous hydrogen peroxide [J].
Chu, Xiaofeng ;
Zhu, Quanjing ;
Dai, Wei-Lin ;
Fan, Kangnian .
RSC ADVANCES, 2012, 2 (18) :7135-7139