Graphene Oxide as Metal-Free Catalyst in the Two-Component Reaction to Generate Some Novel Perimidines and Antimicrobial Evaluation

被引:5
作者
Soni, Jay [1 ]
Sethiya, Ayushi [1 ]
Sahiba, Nusrat [1 ]
Joshi, Deepkumar [2 ]
Agarwal, Shikha [1 ]
机构
[1] Mohanlal Sukhadia Univ, Dept Chem, Synthet Organ Chem Lab, Udaipur, Rajasthan, India
[2] Sheth MN Sci Coll, Dept Chem, Patan, India
关键词
Perimidines; graphene oxide; green synthesis; eco-benign conditions; antimicrobial activity; ORGANIC FRAMEWORK; FACILE SYNTHESIS; EFFICIENT; CARBOCATALYST; COMPLEXES; ZEOLITE;
D O I
10.1080/10406638.2021.2019803
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An eco-friendly, sustainable, simple, and facile protocol has been demonstrated for the synthesis of some novel perimidine derivatives using readily available 1,8-diaminonaphthalene and substituted aldehydes in the presence of green carbocatalyst, graphene oxide (GO). The designed protocol was efficiently carried out under metal-free conditions at room temperature through simple shaking and the desired products were obtained in high to excellent yields in short reaction time (50 sec-2 min) using low catalyst loading (0.005 g). A library of derivatives was synthesized that accomplished high functional group tolerance of the designed protocol. The antimicrobial activity of synthesized compounds was performed against Gram-negative bacteria (E. coli ATCC 25922 and P. aeruginosa ATCC 27853), Gram-positive bacteria (S. aureus ATCC 25923 and B. subtilis ATCC 6633) and fungus (A. niger ATCC 16404) using broth micro dilution method. The present methodology displays many advantages such as high product yields, very less reaction time, wide substrate scope, and simple work-up procedure.
引用
收藏
页码:674 / 685
页数:12
相关论文
共 45 条
[1]   Efficient and simple synthesis of novel 1,2,3-triazolyl-linked benzimidazolone, molecular docking and evaluation of their antimicrobial activity [J].
Adardour, Mohamed ;
Boutafda, Aziz ;
Hdoufane, Ismail ;
Aghraz, Abdellah ;
Hafidi, Mohamed ;
Zaballos-Garcia, Elena ;
Cherqaoui, Driss ;
Baouid, Abdesselam .
SYNTHETIC COMMUNICATIONS, 2020, 50 (22) :3490-3506
[2]   Synthesis and catalytic properties of 1-alkylperimidineruthenium (II) complexes [J].
Alici, B ;
Özdemir, I ;
Karaaslan, K ;
Çetinkaya, E ;
Çetinkaya, B .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2005, 231 (1-2) :261-264
[3]  
Alinezhad H, 2019, J CHEM SCI, V131, DOI 10.1007/s12039-019-1607-8
[4]   Synthesis and antibacterial study of 2-amino-4H-pyrans and pyrans annulated heterocycles catalyzed by sulfated polysaccharide-coated BaFe12O19 nanoparticles [J].
Amirnejat, Sara ;
Nosrati, Aliakbar ;
Peymanfar, Reza ;
Javanshir, Shahrazad .
RESEARCH ON CHEMICAL INTERMEDIATES, 2020, 46 (07) :3683-3701
[5]   Decoration of β-CD-ZrO on Fe3O4 magnetic nanoparticles as a magnetically, recoverable and reusable catalyst for the synthesis of 2,3-dihydro-1H-perimidines [J].
Amrollahi, Mohammad Ali ;
Vahidnia, Fatemeh .
RESEARCH ON CHEMICAL INTERMEDIATES, 2018, 44 (12) :7569-7581
[6]   Synthesis and structural characterization of Pd(II) complexes derived from perimidine ligand and their in vitro antimicrobial studies [J].
Azam, Mohammad ;
Warad, Ismail ;
Al-Resayes, Saud I. ;
Alzaqri, Nabil ;
Khan, Mohammad Rizwan ;
Pallepogu, Raghavaiah ;
Dwivedi, Sourabh ;
Musarrat, Javed ;
Shakir, Mohammad .
JOURNAL OF MOLECULAR STRUCTURE, 2013, 1047 :48-54
[7]   A new catalyst for the synthesis of 2-substituted perimidines catalysed by FePO4 [J].
Behbahani, F. K. ;
Golchin, Fatemeh M. .
JOURNAL OF TAIBAH UNIVERSITY FOR SCIENCE, 2017, 11 (01) :85-89
[8]   A Computational Investigation of the Catalytic Properties of Graphene Oxide: Exploring Mechanisms by using DFT Methods [J].
Boukhvalov, Danil W. ;
Dreyer, Daniel R. ;
Bielawski, Christopher W. ;
Son, Young-Woo .
CHEMCATCHEM, 2012, 4 (11) :1844-1849
[9]   Hemilabile N-Xylyl-N′-methylperimidine Carbene Iridium Complexes as Catalysts for C-H Activation and Dehydrogenative Silylation: Dual Role of N-Xylyl Moiety for ortho-C-H Bond Activation and Reductive Bond Cleavage [J].
Choi, Gyeongshin ;
Tsurugi, Hayato ;
Mashima, Kazushi .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (35) :13149-13161
[10]   Graphene oxide as an acid catalyst for the room temperature ring opening of epoxides [J].
Dhakshinamoorthy, Amarajothi ;
Alvaro, Mercedes ;
Concepcion, Patricia ;
Fornes, Vicente ;
Garcia, Hermenegildo .
CHEMICAL COMMUNICATIONS, 2012, 48 (44) :5443-5445