Dong Zhi-Bing, Gong Zhiying, Dou Qian, Cheng Bin, Wang Taimin
School of Chemistry and Environmental Engineering, Wuhan Institute of Technology, Wuhan 430205, China.
Institute of Marine Biomedicine, Shenzhen Polytechnic, Shenzhen 518055, China.
Org Biomol Chem. 2023 Aug 30;21(34):6806-6829. doi: 10.1039/d3ob00601h.
The diverse synthesis of heterocyclic compounds has always been one of the popular subjects of organic chemistry. To this end, great efforts have been devoted to developing new reagents and establishing new strategies and methods concerning efficiency, selectivity and sustainability. β-Oxodithioesters and their enol tautomers (, α-enolic dithioesters), as a class of simple and readily accessible sulfur-containing synthons, have been widely applied in the construction of various five- and six-membered heterocycles (, thiophenes, thiopyrans, thiazoles, pyridines and quinolines) and other useful open-chain frameworks. Due to their unique chemical structures, β-oxodithioesters bear multiple reaction sites, which enable them to participate in two-component or multicomponent reactions to construct various heterocyclic compounds. In the past decade, the application of β-oxodithioesters in the synthesis of heterocycles has made remarkable progress. Herein, an update on the recent advances in the application of β-oxodithioesters in the synthesis of heterocycles during the period from 2013 to 2023/06 is provided. According to the different types of rings concerning heteroatoms in products, this review is divided into five sections under discussion including (i) synthesis of sulfur-containing heterocycles, (ii) synthesis of sulfur and nitrogen-containing heterocycles, (iii) synthesis of nitrogen-containing heterocycles, (iv) synthesis of nitrogen and oxygen-containing heterocycles, and (v) modification to other open-chain frameworks.
杂环化合物的多样合成一直是有机化学领域热门的课题之一。为此,人们付出了巨大努力来开发新试剂,并建立有关效率、选择性和可持续性的新策略与方法。β-氧代二硫酯及其烯醇互变异构体(α-烯醇式二硫酯)作为一类简单且易于获得的含硫合成子,已被广泛应用于构建各种五元及六元杂环(如噻吩、硫代吡喃、噻唑、吡啶和喹啉)以及其他有用的开链骨架。由于其独特的化学结构,β-氧代二硫酯具有多个反应位点,这使得它们能够参与双组分或多组分反应以构建各种杂环化合物。在过去十年中,β-氧代二硫酯在杂环合成中的应用取得了显著进展。在此,提供了2013年至2023年6月期间β-氧代二硫酯在杂环合成中应用的最新进展。根据产物中杂原子所在环的不同类型,本综述分为五个讨论部分,包括(i)含硫杂环的合成,(ii)含硫和氮杂环的合成,(iii)含氮杂环的合成,(iv)含氮和氧杂环的合成,以及(v)对其他开链骨架的修饰。