N,N -Dialkyl- N′ -Chlorosulfonyl Chloroformamidines in Heterocyclic Synthesis. Part XV. Some Unexpected Reactions with Anilines

Dylan Innes, Michael V. Perkins, Andris J. Liepa, Craig L. Francis

Research output: Contribution to journalArticlepeer-review

Abstract

N,N-Dimethyl-N′-chlorosulfonyl chloroformamidine 1a underwent reactions with various anilines. In addition to the benzo[e][1,2,4]thiadiazine dioxides 8, from 1,3-NCC bis-nucleophilic substitution and bis-anilino adducts 9, some unexpected products were formed, particularly when sterically hindered or electron-poor anilines were used. In these cases, products such as the [1,3,2,4,6]dithiatriazine 1,1,3,3-tetraoxides 17 and, on occasion, N,N,5-trimethyl-4-(arylimino)-4,5-dihydro-[1,3,5]triazin-2-amines 14 were produced in significant yields. Reaction of dichloride 1a with 3-bromoaniline afforded the unusual eight-membered-ring product 2,6-bis(3-bromophenyl)-3,7-bis(dimethylamino)-2H,6H-[1,5,2,4,6,8]dithiatetrazocine 1,1,5,5-tetraoxide 28, in addition to the dithiatriazine tetraoxide 17k. These uncommon heterocyclic structures are of interest for bioactive molecule discovery screening programs.

Original languageEnglish
Pages (from-to)610-623
Number of pages14
JournalAustralian Journal of Chemistry
Volume71
Issue number8
Early online date12 Sep 2018
DOIs
Publication statusPublished - 2018

Keywords

  • Heterocyclic ring systems
  • N,N-Dialkyl-N'
  • Heterocyclic Synthesis
  • Anilines

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