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Diethylaminosulfur Trifluoride: A Novel, Low-Cost, Stable Double Thiolation Reagent for Imidazo[1,2-α]pyridines.

ABSTRACT: We report a novel, inexpensive double thiolation reagent that sulfurizes a broad range of imidazo[1,2-α]pyridines under mild conditions. Importantly, diethylaminosulfur trifluoride, as a common nucleophilic fluorinating reagent, was utilized as a novel thiolation reagent.

SUBMITTER: Jiang H

PROVIDER: S-EPMC8515576 | biostudies-literature | 2021 Oct

REPOSITORIES: biostudies-literature

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Diethylaminosulfur Trifluoride: A Novel, Low-Cost, Stable Double Thiolation Reagent for Imidazo[1,2-α]pyridines.

Jiang Hongmei H Shen Haicheng H Zhu Sha S Wang Binbin B Yang Yujie Y Nong Zhibin Z Yi Min M Tang Shiyun S Gui Qing-Wen QW

ACS omega 20210928 40

We report a novel, inexpensive double thiolation reagent that sulfurizes a broad range of imidazo[1,2-α]pyridines under mild conditions. Importantly, diethylaminosulfur trifluoride, as a common nucleophilic fluorinating reagent, was utilized as a novel thiolation reagent. ...[more]

PMID: 34660986

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Project description:Background?-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(?-bromoacetophenones) with NBS in the presence of p-TsOH in acetonitrile under microwave irradiation is quite novel. The bis- and tris(?-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(?-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(?-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(?-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 ?-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

Diethylaminosulfur Trifluoride: A Novel, Low-Cost, Stable Double Thiolation Reagent for Imidazo[1,2-α]pyridines.

Publications

Diethylaminosulfur Trifluoride: A Novel, Low-Cost, Stable Double Thiolation Reagent for Imidazo[1,2-α]pyridines.

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