Cascade Reaction of Isocyanides with Carboxylic Acid and CD<sub>3</sub>SSO<sub>3</sub>Na: Toward <i>S</i>-CD<sub>3</sub> Thiocarbamates
Xinyu ZhouSchool of Pharmaceutical SciencesKemeng ZhangSchool of Pharmaceutical SciencesShuodan DingSchool of Pharmaceutical SciencesLijin WangSchool of Pharmaceutical SciencesMengtian LiSchool of Pharmaceutical SciencesKe WangSchool of Pharmaceutical SciencesJie ZhouSchool of Pharmaceutical SciencesGe WuChinese Academy of Sciences
2025en
ABI
Аннотация
We developed an unprecedented cascade reaction involving isocyanides with carboxylic acids and CD3SSO3Na to access S-CD3 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 N-alkyl-N-formyl amide followed by thiolation with CD3SSO3Na 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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