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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

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Chemistry of Heterocyclic Compounds Aims and scope

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.

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Correspondence to Alexander A. Shalimov.

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Deceased (Anatoly D. Sinitsa).

Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2016, 52(4), 267–274

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Shalimov, A.A., Chudakova, T.I., Vlasenko, Y.G. et al. Heterocyclization of N-(chlorosulfonyl)imidoyl chlorides with anilines, a new method of synthesis of 1,2,4-benzothiadiazine 1,1-dioxides. Chem Heterocycl Comp 52, 267–274 (2016). https://doi.org/10.1007/s10593-016-1873-z

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