Dataset Information

Ultrasound-Assisted Iodination of Imidazo[1,2-α]pyridines Via C-H Functionalization Mediated by tert-Butyl Hydroperoxide.

ABSTRACT: A novel metal catalyst-free and environmentally friendly method for the regioselective iodination of imidazo[1,2-α]pyridines at their C3 position is disclosed, which has a wide substrate scope and could be sustainable. This reaction proceeds through ultrasound acceleration in the presence of a green alcohol solvent. Compared with a conventional heating system, the reaction efficiency and the rate are significantly improved and the iodine atom economy is maximized using ultrasound techniques.

SUBMITTER: Yang H

PROVIDER: S-EPMC8515396 | biostudies-literature | 2021 Oct

REPOSITORIES: biostudies-literature

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Publications

Ultrasound-Assisted Iodination of Imidazo[1,2-α]pyridines Via C-H Functionalization Mediated by <i>tert</i>-Butyl Hydroperoxide.

Yang Hua H Huang Ning N Wang Nengqing N Shen Haicheng H Teng Fan F Liu Xiaoying X Jiang Hongmei H Tan Mei-Chen MC Gui Qing-Wen QW

ACS omega 20210928 40

A novel metal catalyst-free and environmentally friendly method for the regioselective iodination of imidazo[1,2-α]pyridines at their C3 position is disclosed, which has a wide substrate scope and could be sustainable. This reaction proceeds through ultrasound acceleration in the presence of a green alcohol solvent. Compared with a conventional heating system, the reaction efficiency and the rate are significantly improved and the iodine atom economy is maximized using ultrasound techniques. ...[more]

PMID: 34660956

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Project description:Backgroundα-Bromination of the side chain of aromatic ketones using NBS in the presence of p-toluenesulfonic acid (p-TsOH) in acetonitrile is very common. However, regioselective bromination of bis and tris(ω-bromoacetophenones) with NBS in the presence of p-TsOH in acetonitrile under microwave irradiation is quite novel. The bis- and tris(ω-bromoacetophenones) are used in synthesis of bis and tris(heterocycles). bis(heterocycles) have received a great deal of attention, because many biologically active natural and synthetic products have molecular symmetry. The use of the pressurized microwave irradiation is very advantageous to many syntheses and provide a large rate enhancement.ResultsBis and tris(ω-bromoacetophenones) were obtained as single monobrominated derivatives in a shorter time than the conventional conditions. The results clearly demonstrate the better reactivity and selectivity of NBS/p-TsOH/CH3CN as a brominating mixture under microwave conditions. The reaction of bis and tris(ω-bromoacetophenone) with 2-aminopyridine and 2-aminopyrimidine proceeded smoothly in a mixture of anhydrous ethanol and DMF under reflux or using 300 W/105°C/ 20 min microwave irradiation conditions to afford the corresponding bis(imidazo[1,2-a]pyridine), bis(imidazo[1,2-a]pyrimidine) and tris(imidazo[1,2-a]pyridine) derivatives in moderate to excellent yields. The carbonyl analogue of the targeted bis(imidazopyridines) could be synthesized by the reaction of N,N-dimethyl-N'-(pyridin-2-yl)formimidamide with bis(ω-bromoacetophenone) in refluxing ethanol. The structures of the newly synthesized compounds were confirmed by their spectral data as well as their elemental analyses.ConclusionIn conclusion, selective α-bromination of bis- and tris(acetophenones) has been accomplished efficiently utilizing NBS/p-TsOH/CH3CN under microwave irradiation. In addition, a facile synthesis of novel series of bis- and tris(imidazopyridine) and bis(imidazopyrimidine) derivatives.

Dataset Information

Ultrasound-Assisted Iodination of Imidazo[1,2-α]pyridines Via C-H Functionalization Mediated by tert-Butyl Hydroperoxide.

Publications

Ultrasound-Assisted Iodination of Imidazo[1,2-α]pyridines Via C-H Functionalization Mediated by <i>tert</i>-Butyl Hydroperoxide.

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