An Improved Synthesis of 1λ⁶,2,4,6‐Thiatriazine‐1,3,5‐trione Derivatives – the Sulfonimidamide‐featured Triazinones

Abstract

N,N’‐dicarbamoylation of 4‐methylbenzenesulfon‐imidamide with carbonyldiimidazole, followed by a mono‐nucleophilic substitution with amines and subsequential ring closure in one‐pot, afforded 1λ6,2,4,6‐thiatriazine‐1,3,5‐trione derivatives in up to 83 % yields. The protocol also works well for aliphatic sulfonimidamides, such as methyl sulfonimidamide. The mechanism of formation of both desired and unexpected products is discussed.