An Efficient and Eco-Friendly Protocol for Synthesis of 2-Substituted Benzimidazole and Quinoxaline Derivatives by Using Nanostructured Cu2O as Recyclable Catalyst
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作者:
Kusuma, Suman
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JAIN Univ, Ctr Nano & Mat Sci, Jain Global Campus, Bangalore, Karnataka, India
Aragen Life Sci Pvt Ltd, Bengaluru, IndiaJAIN Univ, Ctr Nano & Mat Sci, Jain Global Campus, Bangalore, Karnataka, India
Kusuma, Suman
[1
,2
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Manjunath, Hemavathi
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JAIN Univ, Ctr Nano & Mat Sci, Jain Global Campus, Bangalore, Karnataka, IndiaJAIN Univ, Ctr Nano & Mat Sci, Jain Global Campus, Bangalore, Karnataka, India
Manjunath, Hemavathi
[1
]
Narayana, Venkat V.
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Venkatsai Life Sci, Hyderabad, Telangana, IndiaJAIN Univ, Ctr Nano & Mat Sci, Jain Global Campus, Bangalore, Karnataka, India
Narayana, Venkat V.
[3
]
Torrejos, Rey Eliseo
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Philippine Text Res Inst, Dept Sci & Technol, Manila, PhilippinesJAIN Univ, Ctr Nano & Mat Sci, Jain Global Campus, Bangalore, Karnataka, India
Torrejos, Rey Eliseo
[4
]
Norrrahim, Mohd Nor Faiz
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Univ Pertahanan Nasl Malaysia UPNM, Res Ctr Chem Def, Kuala Lumpur, MalaysiaJAIN Univ, Ctr Nano & Mat Sci, Jain Global Campus, Bangalore, Karnataka, India
Norrrahim, Mohd Nor Faiz
[5
]
Jadhav, Arvind H.
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JAIN Univ, Ctr Nano & Mat Sci, Jain Global Campus, Bangalore, Karnataka, IndiaJAIN Univ, Ctr Nano & Mat Sci, Jain Global Campus, Bangalore, Karnataka, India
Jadhav, Arvind H.
[1
]
机构:
[1] JAIN Univ, Ctr Nano & Mat Sci, Jain Global Campus, Bangalore, Karnataka, India
[2] Aragen Life Sci Pvt Ltd, Bengaluru, India
[3] Venkatsai Life Sci, Hyderabad, Telangana, India
[4] Philippine Text Res Inst, Dept Sci & Technol, Manila, Philippines
[5] Univ Pertahanan Nasl Malaysia UPNM, Res Ctr Chem Def, Kuala Lumpur, Malaysia
1,2-diketone reaction;
benzimidazole;
Cu2O cube catalyst;
heterocyclic synthesis;
o-phenylenediamine;
quinoxaline synthesis;
ONE-POT SYNTHESIS;
FACILE ONE-POT;
CUPROUS-OXIDE NANOPARTICLES;
N BOND FORMATION;
1,2-DISUBSTITUTED BENZIMIDAZOLES;
MOLECULAR-IODINE;
C-N;
CO2;
MILD;
CYCLIZATION;
D O I:
10.1002/aoc.70038
中图分类号:
O69 [应用化学];
学科分类号:
081704 ;
摘要:
Reconnoitre the use of earth-abundant metals for an essential organic reaction was extremely provocative from an industrial vantage point. In this study, the fundamental and energy-efficient co-precipitation approach was employed to aid the Cu2O cubed nanostructured catalyst in the generation of benzimidazole and quinoxaline derivatives. The developed Cu2O cubed nanostructured catalyst was thoroughly evaluated by world-class analytical and spectroscopic techniques. The Cu2O cube catalyst exhibited exceptional crystallinity, a cubic shape, a large specific surface area and uniformly distributed active sites on its surface. The obtained astounding structural and physico-chemical characteristics successfully enabled the catalytic activity for the synthesis of benzimidazole and quinoxaline. The recognised vital structural and physical attributes substantially improved the catalytic activity for the production of benzimidazole and quinoxaline derivatives over mild reaction conditions. Employing a cubic Cu2O catalyst, diverse reaction parameters have been examined, encompassing the effects of catalyst dosage, temperature, time, solvent, yield and substrate scope. As a result, the designed catalyst was used to synthesise heterocyclic 2-substituted benzimidazole and quinoxaline derivatives via the condensation of o-phenylenediamine, aldehydes and 1,2-diketone. The reported results showed 100% conversion in both aimed products, with 90% selectivity for 2-substituted benzimidazole and 95% selectivity for quinoxaline derivatives, respectively. The obtained yield for 2-substituted benzimidazole and quinoxaline derivatives was 85 and 98 at 60 degrees C for 3 and 4 h, individually. The catalytic activity was fully based on the inherent properties of cubic Cu2O . On top of that, all synthesised compounds were structurally validated by 1H NMR, 13C NMR and mass spectrum data. Remarkably, the efficient cubic Cu2O catalyst demonstrated impressive recyclability for up to six consecutive cycles with minimal loss of its initial catalytic activity. The spent cubic Cu2O catalyst's characteristic results revealed evidence for its stable structural and physico-chemical features. In addition, we endeavoured to propose and describe a plausible reaction mechanism utilizing the developed nanostructured Cu2O cubes for the synthesis of benzimidazole and quinoxaline derivatives.
机构:
Islamic Azad Univ, Dept Chem, Ayatollah Amoli Branch, Amol, IranIslamic Azad Univ, Dept Chem, Ayatollah Amoli Branch, Amol, Iran
Vahdat, Seyed Mohammad
Baghery, Saeed
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机构:
Bu Ali Sina Univ, Coll Sci, Dept Chem, Hamadan, Iran
Islamic Azad Univ, Ayatollah Amoli Branch, Young Res Club, Amol, IranIslamic Azad Univ, Dept Chem, Ayatollah Amoli Branch, Amol, Iran
机构:
Department of Chemistry,Dr.Babasaheb Ambedkar Marathwada University,Aurangabad,Maharashtra 431 004,India
Division of Medicinal Chemistry,Wockhardt Research Centre,D-4,Chikalthana M.I.D.C.Area,Aurangabad,Maharashtra 431 210,IndiaDepartment of Chemistry,Dr.Babasaheb Ambedkar Marathwada University,Aurangabad,Maharashtra 431 004,India
Ganesh R.Jadhav
Mohammad U.Shaikh
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机构:
Division of Medicinal Chemistry,Wockhardt Research Centre,D-4,Chikalthana M.I.D.C.Area,Aurangabad,Maharashtra 431 210,IndiaDepartment of Chemistry,Dr.Babasaheb Ambedkar Marathwada University,Aurangabad,Maharashtra 431 004,India
Mohammad U.Shaikh
Rajesh P.Kale
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机构:
Division of Medicinal Chemistry,Wockhardt Research Centre,D-4,Chikalthana M.I.D.C.Area,Aurangabad,Maharashtra 431 210,IndiaDepartment of Chemistry,Dr.Babasaheb Ambedkar Marathwada University,Aurangabad,Maharashtra 431 004,India
Rajesh P.Kale
Charansingh H.Gill
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机构:
Department of Chemistry,Dr.Babasaheb Ambedkar Marathwada University,Aurangabad,Maharashtra 431 004,IndiaDepartment of Chemistry,Dr.Babasaheb Ambedkar Marathwada University,Aurangabad,Maharashtra 431 004,India