Hu Kai-Wen, You Xiao, Wen Xiaoan, Yuan Haoliang, Xu Qing-Long, Lai Zengwei
School of Life Sciences and Health Engineering, Jiangnan University,1800 Lihu Avenue, 214122, Wuxi, China.
Jiangsu Key Laboratory of Drug Discovery for Metabolic Diseases and State Key Laboratory of Natural Medicines, China Pharmaceutical University, 24 Tongjia Xiang, Nanjing 210009, China.
J Org Chem. 2023 Apr 21;88(8):5052-5058. doi: 10.1021/acs.joc.2c01031. Epub 2022 Jul 26.
An efficient and environmentally friendly synthetic approach to prepare thiazolidine-2-imine and oxazolidine-2-one derivatives has been developed. Thiazolidine-2-imines are synthesized in good to excellent yields by [3 + 2] annulation of -quinamines with isothiocyanates under catalyst- and solvent-free conditions. Oxazolidine-2-ones are produced in good to excellent yields via [3 + 2] annulation of -quinamines with CO using triethylenediamine (DABCO) as an organocatalyst. Furthermore, this strategy can be performed on a gram scale and tolerate a wide range of functional groups.
已开发出一种高效且环保的合成方法来制备噻唑烷-2-亚胺和恶唑烷-2-酮衍生物。在无催化剂和无溶剂条件下，通过喹胺与异硫氰酸酯的[3 + 2]环化反应，以良好至优异的产率合成了噻唑烷-2-亚胺。使用三亚乙基二胺（DABCO）作为有机催化剂，通过喹胺与CO的[3 + 2]环化反应，以良好至优异的产率制备了恶唑烷-2-酮。此外，该策略可在克级规模上进行，并且能耐受多种官能团。
