Cascade Reaction of Isocyanides with Carboxylic Acid and CDSSONa: Toward -CD Thiocarbamates.
作者信息
Zhou Xinyu, Zhang Kemeng, Ding Shuodan, Wang Lijin, Li Miaoying, Wang Ke, Zhou Jie, Wu Ge
机构信息
School of Pharmaceutical Sciences, Wenzhou Medical University, Wenzhou 325035, China.
State Key Laboratory of Structural Chemistry, Fujian Institute of Research on the Structure of Matter, Chinese Academy of Sciences, Fuzhou, Fujian 350002, China.
出版信息
Org Lett. 2025 May 9;27(18):4742-4746. doi: 10.1021/acs.orglett.5c01166. Epub 2025 Apr 29.
We developed an unprecedented cascade reaction involving isocyanides with carboxylic acids and CDSSONa to access -CD thiocarbamates with the formation of two C-N bonds and one C-S bond. Preliminary mechanistic investigations disclose that these three-component reactions precede the esterification of carboxylic acids with isocyanides, generating a capable -alkyl--formyl amide followed by thiolation with CDSSONa to provide the corresponding products. The transformation has outstanding features in mild reaction conditions, effortless experimental operation, structural modification of polyfunctional carboxylic acid drugs, and large-scale preparation.
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