β-Cyclodextrin-promoted synthesis of 2-phenylbenzimidazole in water using air as an oxidant

Ji, Hongbing; Huang, Liquan; Shen, Hai‐Min; Zhou, Xiantai

doi:10.1016/j.cej.2010.12.084

Cited by 10 publications

(2 citation statements)

References 39 publications

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“…It is interesting that a high yield was still obtained by using β-CD as a catalyst in the absence of a base in this study. Ji et al reported that β-CD could improve the synthesis of 2-phenylbezimidazole using air as an oxidant, since the oxidative cyclodehydrogenation of the Schiff base intermediates was promoted inside the β-CD cavity [29]. Therefore, it is supposed that the mechanism of β-CD catalysis in this study is also due to the promotion of oxidative cyclodehydrogenation.…”

Section: Resultsmentioning

confidence: 66%

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Green Synthesis of Indeno[1,2-b]quinoxalines Using β-Cyclodextrin as Catalyst

et al. 2022

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An efficient, mild, and green method was developed for the synthesis of indeno[1,2-b]quinoxaline derivatives via o-phenylenediamine (OPD) and 2-indanone derivatives utilizing β-cyclodextrin (β-CD) as the supramolecular catalyst. The reaction can be carried out in water and in a solid state at room temperature. β-CD can also catalyze the reaction of indan-1,2-dione with OPD with a high degree of efficiency. Compared to the reported methods, this procedure is milder, simpler, and less toxic, making it an eco-friendly alternative. In addition, the β-CD can be recovered and reused without the loss of activity.

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Section: Resultsmentioning

confidence: 66%

“…Based on the above data and the reports documented in the literature [29][30][31][32], a plausible reaction mechanism is proposed in Scheme 2. First, OPD is included in the cavity of β-CD to form the OPD-β-CD inclusion complex.…”

Section: Resultsmentioning

confidence: 72%

Green Synthesis of Indeno[1,2-b]quinoxalines Using β-Cyclodextrin as Catalyst

et al. 2022

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Interaction of β-cyclodextrin as catalyst with acetophenone in asymmetric reaction: a theoretical survey

2014

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The asymmetric reduction of acetophenone with sodium borohydride in the presence of β-cyclodextrin (β-CD) as catalyst can improve selectivity and yield. The interaction between acetophenone and β-CD plays an important role for the reduction of acetophenone. This work studies the reaction of acetophenone in the presence of β-CD using density functional theory (DFT) method. Energy is investigated to find out the lowest energy of two possible complexation models. The geometrical structure confirms that acetophenone inserts into the cavity mainly from the secondary hydroxyl side. Hydrogen bonds are researched on the basis of natural bonding orbital (NBO) analysis, the results confirm the donor-acceptor interactions of complex. Mülliken charge and frontier orbital are employed for revealing the electronic transfer. In addition, (13)C nuclear magnetic resonance ((13)CNMR) spectroscopy shows that the active site concentrates on the carbon atom of carbonyl group. The probable catalytic mechanism of β-CD is discussed in terms of the calculated parameters.

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DFT study of the per-6-amino-β-cyclodextrin as catalyst in synthesis of 2-aryl-2,3-dihydro-4-quinolones

2014

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The synthesis of 2-aryl-2,3-dihydro-4-quinolones in the presence of per-6-amino-β-cyclodextrin (per-6-ABCD) as catalyst can improve selectivity and yield. The interaction between per-6-ABCD and benzaldehyde or o-aminoacetophenone plays an important role in this reaction. This paper studies the complexes of per-6-ABCD with benzaldehyde and o-aminoacetophenone using density functional theory (DFT) method. The reaction process is investigated by studying the energy of the reactants and the product. Hydrogen bonds are researched on the basis of natural bonding orbital (NBO) analysis, the results propose the donor-acceptor interactions of complex. The Mulliken charge and frontier orbital are employed for revealing the charge distribution. In addition, (13)C nuclear magnetic resonance ((13)CNMR) spectroscopy shows that the carbon atom on the aldehyde group for benzaldehyde, carbonyl group and the carbon atom connected with carbonyl group for o-aminoacetophenone are apparently activated in the cavity of per-6-ABCD. The probable catalytic mechanism of per-6-ABCD is discussed in terms of the calculated parameters.

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β-Cyclodextrin-promoted synthesis of 2-phenylbenzimidazole in water using air as an oxidant

Cited by 10 publications

References 39 publications

Green Synthesis of Indeno[1,2-b]quinoxalines Using β-Cyclodextrin as Catalyst

Green Synthesis of Indeno[1,2-b]quinoxalines Using β-Cyclodextrin as Catalyst

Interaction of β-cyclodextrin as catalyst with acetophenone in asymmetric reaction: a theoretical survey

DFT study of the per-6-amino-β-cyclodextrin as catalyst in synthesis of 2-aryl-2,3-dihydro-4-quinolones

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