One pot multicomponent synthesis of highly substituted imidazoles using tetrabutylammonium peroxy disulfate as a catalyst

被引:5
|
作者
Nukala, Ramesh [1 ]
Gullapelli, Kumaraswamy [2 ]
Konakanchi, Ramaiah [3 ]
机构
[1] Indian Inst Chem Technol, OSPC Div, Hyderabad 500607, India
[2] Mahatma Gandhi Inst Technol, Dept Chem, Hyderabad 500075, India
[3] VNR Vignana Jyothi Inst Engn & Technol, Dept Humanities & Sci Chem, Hyderabad 500090, India
关键词
Synthesis; Imidazoles; Tetra butyl ammonium peroxy disulfate; Catalysis; 4-COMPONENT SYNTHESIS; GREEN; DERIVATIVES; PYRAZOLE; FACILE;
D O I
10.1007/s11164-023-05090-8
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A fascinating trend in the synthesis of heterocyclic molecules is focused on green chemistry, including efficient reactions and the use of eco-friendly reagents to meet the demands of the pharmaceutical industry due to its many biological activities. In our ongoing efforts to promote new synthetic strategies for preparing heterocyclic compounds in this study. In this work describes a method for the synthesis of tri- and tetra-substituted imidazoles using Tetra butyl ammonium Peroxy disulfate (TBAPDS) as a catalyst. The reaction involves a multi-component condensation of benzoin, aniline, ammonium acetate, and araldehydes in acetonitrile under reflux conditions similar to 2 to 3 h at 60-65 degrees C. Results found that optimized 20% mole ratio of TBAPDS catalyst to acetonitrile solvent resulted in excellent yields of the desired products (77-96%). The use of TBAPDS as a catalyst in this condensation reaction offers several advantages, including operational simplicity, cost-effectiveness, reusability of the catalyst, and high product yields. To confirm the structures of the newly synthesized compounds, various spectroscopic techniques were employed. Proton-NMR, C-13-NMR, FTIR, and mass spectra were used to analyze and characterize the chemical structures of the synthesized imidazoles. (HNMR)-H-1 data reveals that all aromatic protons were present in that at chemical shift value delta 6.92-7.89 ppm. Overall, the study highlights a simple and efficient method for the synthesis of tri- and tetra-substituted imidazoles using TBAPDS as a catalyst. The results suggest that this method holds promise for the production of these compounds, offering advantages such as cost-effectiveness and high yields.
引用
收藏
页码:4713 / 4727
页数:15
相关论文
共 50 条
  • [41] Citric acid, a green catalyst for the one-pot, multi-component synthesis of highly substituted piperidines
    Madanifar, Zahra
    Maghsoodlou, Malek-Taher
    Kangani, Mehrnoosh
    Hazeri, Nourallah
    RESEARCH ON CHEMICAL INTERMEDIATES, 2015, 41 (12) : 9863 - 9869
  • [42] One-Pot Multicomponent Reactions for the Efficient Synthesis of Highly Functionalized Dihydropyridines
    Pal, Suman
    Choudhury, Lokman H.
    Parvin, Tasneem
    SYNTHETIC COMMUNICATIONS, 2013, 43 (07) : 986 - 992
  • [43] Facile one-pot multicomponent synthesis of highly functionalized tetrahydropyridines using thiamine hydrochloride as an organocatalyst
    Singh, Sandeep
    Gupta, Annah
    Kapoor, Kamal K.
    SYNTHETIC COMMUNICATIONS, 2020, 50 (07) : 1056 - 1063
  • [44] Highly efficient, one-pot, solvent-free synthesis of tetrasubstituted imidazoles using HClO4-SiO2 as novel heterogeneous catalyst
    Kantevari, Srinivas
    Vuppalapati, Srinivasu V. N.
    Biradar, Dhanraj O.
    Nagarapu, Lingaiah
    JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2007, 266 (1-2) : 109 - 113
  • [45] Highly efficient methods for the one-pot synthesis of β-substituted enones
    Kerr, WJ
    Pearson, CM
    Thurston, GJ
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2006, 4 (01) : 47 - 50
  • [46] One-pot synthesis of new highly substituted allylic phosphorodiamidates
    Bahri, Leila
    Barhoumi-Slimi, T.
    Mallek, R.
    Sanhoury, M. A. K.
    Crousse, B.
    Ben Dhia, M. T.
    JOURNAL OF FLUORINE CHEMISTRY, 2016, 189 : 96 - 101
  • [47] Stereoselective one-pot synthesis of highly differently substituted thiochromans
    Seifert, Andrea
    Mahrwald, Rainer
    TETRAHEDRON LETTERS, 2009, 50 (47) : 6466 - 6468
  • [48] Expeditious and Highly Efficient One-Pot Synthesis of Functionalized Imidazoles Catalyzed by Sulfated Polyborate
    Indalkar, Krishna
    Malge, Sanjay S.
    Mali, Anil S.
    Chaturbhuj, Ganesh U.
    ORGANIC PREPARATIONS AND PROCEDURES INTERNATIONAL, 2021, 53 (04) : 387 - 396
  • [49] One-pot synthesis of highly substituted poly(furopyrimidine)s via catalyst-free multicomponent polymerizations of diisocyanides, N,N′-dimethylbarbituric acid, and dialdehyde
    Dong, Lichao
    Li, Nan
    Yuan, Hang
    Wu, Meng
    RSC ADVANCES, 2022, 12 (10) : 6347 - 6351
  • [50] Boehmite nanoparticles, an efficient green catalyst for the multi-component synthesis of highly substituted imidazoles
    Keivanloo, Ali
    Bakherad, Mohammad
    Imanifar, Elahe
    Mirzaee, Mahdi
    APPLIED CATALYSIS A-GENERAL, 2013, 467 : 291 - 300