Alkyl Ether as a One-Carbon Synthon: Route to 2,4-Disubstituted 1,3,5-Triazines via C–H Amination/C–O Cleavage under Transition-Metal-Free Conditions

• DOI: 10.1021/acs.orglett.7b03171
• Publication Date: 2017-11-03T13:08:17Z
• Authors: Yizhe Yan; Zheng Li; Hongyi Li; Chang Cui; Miaomiao Shi; Yanqi Liu
• Keywords: Synthon; Aromatization; Bond cleavage

A transition-metal-free oxidative formal [3 + 2 1] cycloaddition for the synthesis of symmetrical and unsymmetrical 2,4-disubstituted 1,3,5-triazines has been first demonstrated. The reaction is involved in a domino C–H amination alkyl ethers with amidines, C–O cleavage, nucleophilic addition, condensation, an aromatization process. Notably, two C–N bonds were constructed one pot, employed as novel carbon source 1,3,5-triazines. preliminary mechanistic studies revealed underwent radical pathway.