Sequential One-Pot Synthesis of Diversely Functionalized 1,3,5-Triazines via Cyanuric Chloride with Amino Groups and Boronic Acids

A cyanuric chloride-mediated sequential one-pot strategy enables the rapid construction of trisubstituted 1,3,5-triazines via three C-N or two C-N with one C-C bond formations. By delicately designing the sequence of reagent addition, this operationally simple protocol exhibits broad functional group tolerance across 22 examples (34-69% yield) performed from milligram to subgram quantities and demonstrates future derivatizations. Finally, the synthetic utility is highlighted by the successful synthesis of the FDA-approved anticancer drug Enasidenib.