Beckmann rearrangement of ketoximes promoted by cyanuric chloride and dimethyl sulfoxide under a mild condition

DOI: 10.1016/j.tetlet.2020.152707

Source and publish data:

Tetrahedron Letters (2021)

Update date:2022-09-26

Topics:

Authors:

Ma, Ruonan

Chen, Xueyuan

Xiao, Zhiyin

Natarajan, Mookan

Lu, Chunxin

Jiang, Xiujuan

Zhong, Wei

Liu, Xiaoming

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Article abstract of DOI:10.1016/j.tetlet.2020.152707

Synthesis of amides via Beckmann rearrangement of ketoximes promoted by cyanuric chloride (TCT)/DMSO under mild conditions has been reported. Conditions of the Beckmann rearrangement, e.g., solvents, the ratios of TCT/DMSO, and the temperature, were investigated using diphenylmethanone oxime as a substrate. The optimized conditions were adopted to afford fourteen amides with yields ranging from 20% to 99%. A plausible mechanism involving an active dimethyl alkoxysulfonium intermediate was proposed according to the mass spectrometry analysis. To our best knowledge, this is the first case of study on Beckmann rearrangement of ketoximes promoted by TCT/DMSO under a mild condition to afford amides efficiently.

Full text of DOI:10.1016/j.tetlet.2020.152707

Journal Pre-proofs

Beckmann rearrangement of ketoximes promoted by cyanuric chloride and di‐

methyl sulfoxide under a mild condition

Ruonan Ma, Xueyuan Chen, Zhiyin Xiao, Mookan Natarajan, Chunxin Lu,

Xiujuan Jiang, Wei Zhong, Xiaoming Liu

PII:

S0040-4039(20)31218-1

DOI:

Reference:

https://doi.org/10.1016/j.tetlet.2020.152707

TETL 152707

To appear in:

Tetrahedron Letters

Received Date:

Revised Date:

Accepted Date:

31 August 2020

5 November 2020

23 November 2020

Please cite this article as: Ma, R., Chen, X., Xiao, Z., Natarajan, M., Lu, C., Jiang, X., Zhong, W., Liu, X.,

Beckmann rearrangement of ketoximes promoted by cyanuric chloride and dimethyl sulfoxide under a mild

condition, Tetrahedron Letters (2020), doi: https://doi.org/10.1016/j.tetlet.2020.152707

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Tetrahedron Letters, Journal Pre-proof, 152707. doi:10.1016/j.tetlet.2020.152707

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