HETEROCYCLIZATION OF <i>N</i>-(CHLOROSULFONYL)IMIDOYL CHLORIDES WITH ANILINES, A NEW METHOD OF SYNTHESIS OF 1,2,4-BENZOTHIADIAZINE 1,1-DIOXIDES

Authors

  • Александр А. Шалимов Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 5 Murmanska St., Kyiv 02094
  • Татьяна И. Чудакова Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 5 Murmanska St., Kyiv 02094
  • Юрий Г. Власенко Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 5 Murmanska St., Kyiv 02094
  • Анатолий Д. Синица
  • Петр П. Онысько Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 5 Murmanska St., Kyiv 02094

DOI:

https://doi.org/10.1007/3109

Keywords:

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

Abstract

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 С-2 and С-6 atoms of aniline.

Authors: Alexander A. Shalimov*, Tetyana I. Chudakova, Yurii G. Vlasenko, Anatoly D. Sinitsa†, Petro P. Onys'ko

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Published

2016-04-28

Issue

Vol. 52 No. 4 (2016)

Section

Original Papers