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Synthesis of pyrrole disulfides via umpolung of ß-ketothioamides.
Meng, Xiangrui; Guo, Weisi; Nan, Guangming; Li, Ming.
Affiliation
  • Meng X; Key Lab of Natural Product Chemistry and Application in Xinjiang, School of Chemistry and Environmental Science, Yili Normal University, Yining 835000, P. R. China. nanguangming02@sohu.com.
  • Guo W; College of Chemistry and Molecular Engineering, Qingdao University of Science and Technology, Qingdao 266042, P. R. China. liming928@qust.edu.cn.
  • Nan G; Key Lab of Natural Product Chemistry and Application in Xinjiang, School of Chemistry and Environmental Science, Yili Normal University, Yining 835000, P. R. China. nanguangming02@sohu.com.
  • Li M; Key Lab of Natural Product Chemistry and Application in Xinjiang, School of Chemistry and Environmental Science, Yili Normal University, Yining 835000, P. R. China. nanguangming02@sohu.com.
Org Biomol Chem ; 20(38): 7609-7612, 2022 10 05.
Article in En | MEDLINE | ID: mdl-36156622
ABSTRACT
A Na2CO3-promoted reaction of ß-ketothioamides (KTAs) and cyanoacetates was developed for the synthesis of pyrrole disulfides using air as a green oxidant. This protocol features a broad substrate scope and mild reaction conditions. Preliminary mechanistic studies indicate that the reaction involves a tandem unusual umpolung of KTAs, N-cyclization, tautomerization and oxidative coupling process.
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Full text: 1 Collection: 01-internacional Database: MEDLINE Main subject: Pyrroles / Disulfides Language: En Journal: Org Biomol Chem Journal subject: BIOQUIMICA / QUIMICA Year: 2022 Type: Article
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Full text: 1 Collection: 01-internacional Database: MEDLINE Main subject: Pyrroles / Disulfides Language: En Journal: Org Biomol Chem Journal subject: BIOQUIMICA / QUIMICA Year: 2022 Type: Article