Pali Pragya, Shukla Gaurav, Saha Priya, Singh Maya Shankar
Department of Chemistry, Institute of Science, Banaras Hindu University, Varanasi 221005, India.
Org Lett. 2021 May 21;23(10):3809-3813. doi: 10.1021/acs.orglett.1c00766. Epub 2021 May 6.
An operationally simple and sustainable one-pot photo-oxidative formal [3 + 2] heterocyclization of β-ketothioamides with aryldiazonium salts catalyzed by Ru(bpy)Cl 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 α-phenylhydrazone adduct of thioamides leading to 1,2,3-thiadiazoles via N-S bond formation at room temperature. Notably, the products possess -stereochemistry with regard to the exocyclic C═N double bond at the 5-position of the ring.
首次实现了在温和反应条件下，由Ru(bpy)Cl催化的β-酮硫代酰胺与芳基重氮盐进行的操作简单且可持续的一锅光氧化形式[3 + 2]杂环化反应，以良好至高产率得到2,4-二取代的5-亚氨基-1,2,3-噻二唑。该反应通过硫代酰胺的α-苯腙加合物进行，在室温下通过N-S键形成生成1,2,3-噻二唑。值得注意的是，产物在环5位的环外C═N双键方面具有立体化学结构。
