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

Александр А. Шалимов, Татьяна И. Чудакова, Юрий Г. Власенко, Анатолий Д. Синица, Петр П. Онысько
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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


Keywords


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

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