Chemistry of Heterocyclic Compounds

, Volume 52, Issue 4, pp 267–274 | Cite as

Heterocyclization of N-(chlorosulfonyl)imidoyl chlorides with anilines, a new method of synthesis of 1,2,4-benzothiadiazine 1,1-dioxides

  • Alexander A. Shalimov
  • Tetyana I. Chudakova
  • Yurii G. Vlasenko
  • Anatoly D. Sinitsa
  • Petro P. Onys’ko
Article
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N-(Chlorosulfonyl)imidoyl chlorides react regioselectively with anilines, 2-aminomethylnaphthaline, or 1,2,3,4-tetrahydroquinoline leading to derivatives of 1,2,4-benzothiadiazine 1,1-dioxide. Heterocyclization occurs at the sterically less hindered C-6 atom in the case of 3-methoxy- and 3,4-dimethoxyaniline, while the reaction with 3-methylaniline leads to a mixture of cyclization products at the C-2 and C-6 atoms of aniline.

Keywords

anilines 1,2,4-benzothiadiazine 1,1-dioxides imidoyl chlorides sulfonyl chlorides heterocyclization 
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Copyright information

© Springer Science+Business Media New York 2016

Authors and Affiliations

  • Alexander A. Shalimov
    • 1
  • Tetyana I. Chudakova
    • 1
  • Yurii G. Vlasenko
    • 1
  • Anatoly D. Sinitsa
    • 1
  • Petro P. Onys’ko
    • 1
  1. 1.Institute of Organic ChemistryNational Academy of Sciences of UkraineKyivUkraine

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