Access to Imidazolidines via 1,3-Dipolar Cycloadditions of 1,3,5-Triazinanes with Aziridines

• DOI: 10.1021/acs.joc.9b01959
• Publication Date: 2019-07-29T12:28:08Z
• Authors: Liang Tu; Zhenghui Li; Tao Feng; Shuyan Yu; Rong Huang; Jing Li; Wenxuan Wang; Yongsheng Zheng; Jikai Liu
• Keywords: 01 natural sciences; 0104 chemical sciences

The unprecedented 1,3-dipolar cycloaddition of 1,3,5-triazinanes and aziridines has been described. With readily available starting material, this method offers efficient access to a wide range of functionalized imidazolidine derivatives in moderate to good yields (up to 92%) under mild conditions. Preliminary mechanistic investigations show that the ring opened zwitterionic pathway product dominated over the second-order nucleophilic substitution-like product. This protocol is very promising because the reaction is scalable, and gives versatile transformation of the products into other functionalized imidazolidines.