539-03-7Relevant articles and documents
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Mills
, (1862)
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Southwick et al.
, p. 101,103 (1956)
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Transamidation and Decarbonylation of N-Phthaloyl-Amino Acid Amides Enabled by Palladium-Catalyzed Selective C–N Bond Cleavage
Zhang, Hao-Yu,Tao, Xuan-Wen,Yi, Li-Na,Zhao, Zhi-Gang,Yang, Qiang
, p. 231 - 242 (2022/01/11)
Amides are important functional synthons that have been widely used in the construction of peptides, natural products, and drugs. The C–N bond cleavage provides the direct method for amide conversion. However, amides, especially secondary amides, tend to
Method for promoting acylation of amine or alcohol by carbon dioxide
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Paragraph 0033-0034, (2021/05/29)
The invention relates to a method for promoting acylation of amine or alcohol by carbon dioxide, which comprises the following steps of: mixing an amine compound, carboxylate or thiocarboxylate compound and a reaction solvent under the action of carbon dioxide, and reacting to obtain an amide compound, or under the action of carbon dioxide, mixing the alcohol compound, the thiocarboxylate compound and the reaction solvent [gamma]-valerolactone, and reacting to obtain the ester compound. According to the invention, under the promotion action of carbon dioxide, carboxylate or thiocarboxylate is used as an acylation reagent, and amine and alcohol are converted into amide and ester compounds in the absence of a transition metal catalyst, so that acylation reagents such as acyl chloride or anhydride with irritation and corrosivity are avoided; and the method has the advantages of simple operation, mild reaction conditions, high tolerance of substrate functional groups, strong applicability and high yield, and provides an efficient, reliable and economical preparation method for synthesis of amide and ester compounds.
Beckmann rearrangement of ketoximes promoted by cyanuric chloride and dimethyl sulfoxide under a mild condition
Ma, Ruonan,Chen, Xueyuan,Xiao, Zhiyin,Natarajan, Mookan,Lu, Chunxin,Jiang, Xiujuan,Zhong, Wei,Liu, Xiaoming
supporting information, (2021/01/06)
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.