4.8 Article

Photo-oxidative Ruthenium(II)-Catalyzed Formal [3+2] Heterocyclization of Thioamides to Thiadiazoles

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ORGANIC LETTERS
卷 23, 期 10, 页码 3809-3813

出版社

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c00766

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资金

  1. Science and Engineering Research Board [CRG/2019/000058]
  2. Council of Scientific and Industrial Research [02(0348)/19/EMR-II]
  3. JC Bose National Fellowship, New Delhi [JCB/2020/000023]
  4. UGC & SERB, New Delhi

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An operationally simple and sustainable one-pot photo-oxidative formal [3 + 2] heterocyclization of beta-ketothioamides with aryldiazonium salts catalyzed by Ru(bpy)(3)Cl-2 has been realized to provide 2,4-disubstituted 5-imino-1,2,3-thiadiazoles in good to high yields under mild reaction conditions for the first time. The reaction proceeded via an a-phenylhydrazone adduct of thioamides leading to 1,2,3-thiadiazoles via N-S bond formation at room temperature. Notably, the products possess Z-stereochemistry with regard to the exocyclic C = N double bond at the 5-position of the ring.
An operationally simple and sustainable one-pot photo-oxidative formal [3 + 2] heterocyclization of beta-ketothioamides with aryldiazonium salts catalyzed by Ru(bpy)(3)Cl-2 has been realized to provide 2,4-disubstituted 5-imino-1,2,3-thiadiazoles in good to high yields under mild reaction conditions for the first time. The reaction proceeded via an a-phenylhydrazone adduct of thioamides leading to 1,2,3-thiadiazoles via N-S bond formation at room temperature. Notably, the products possess Z-stereochemistry with regard to the exocyclic C = N double bond at the 5-position of the ring.

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