A multistep reaction of 5-halo-1,2,3-thiadiazoles and 1,2-phenylenediamines provides a new route to fused 1,3,6-thiadiazepines. The overall process consists of the known stepwise formation of 5-[1-(2-aminophenyl)-1,2,3-triazol-5-ylsulfanyl]-1,2,3-thiadiazole, and a novel ring transformation which involves the Smiles and Dimroth rearrangements followed by an intramolecular nucleophilic substitution of the thiol group, affording di[1,2,3]triazolo[1,5-a:5′,1′-d][3,1,5]benzothiadiazepines. The influence of the substituents on the 1,2,3-thiadiazole and phenyl rings on this reaction was discussed.
通过 5-卤基-1,2,3-
噻二唑和 1,2-
苯二胺的多步反应,提供了一条获得融合型 1,3,6-噻二氮杂卓的新途径。整个过程包括已知的 5-[1-(2-
氨基苯基)-
1,2,3-三唑-5-基
硫基]-1,2,3-
噻二唑的逐步形成,以及一种新的环状转化,其中涉及 Smiles 和 Dimroth 重排,然后是
硫醇基团的分子内亲核取代,从而得到二[1,2,3]三唑并[1,5-a:5′,1′-d][3,1,5]苯并噻二氮杂卓。讨论了 1,2,3-
噻二唑和苯基环上的取代基对该反应的影响。