Regioselective synthesis of heterocyclic N-sulfonyl amidines from heteroaromatic thioamides and sulfonyl azides. 2020

Vladimir Ilkin, and Vera Berseneva, and Tetyana Beryozkina, and Tatiana Glukhareva, and Lidia Dianova, and Wim Dehaen, and Eugenia Seliverstova, and Vasiliy Bakulev
TOS Department, Ural Federal University named after the first President of Russia B.N. Yeltsin, 19 Mira St., 620002 Yekaterinburg, Russia.

N-Sulfonyl amidines bearing 1,2,3-triazole, isoxazole, thiazole and pyridine substituents were successfully prepared for the first time by reactions of primary, secondary and tertiary heterocyclic thioamides with alkyl- and arylsulfonyl azides. For each type of thioamides a reliable procedure to prepare N-sulfonyl amidines in good yields was found. Reactions of 1-aryl-1,2,3-triazole-4-carbothioamides with azides were shown to be accompanied with a Dimroth rearrangement to form 1-unsubstituted 5-arylamino-1,2,3-triazole-4-N-sulfonylcarbimidamides. 2,5-Dithiocarbamoylpyridine reacts with sulfonyl azides to form a pyridine bearing two sulfonyl amidine groups.

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