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

Ilkin, V.; Berseneva, V.; Beryozkina, T.; Glukhareva, T.; Dianova, L.; Dehaen, W.; Seliverstova, E.; Bakulev, V.

Beilstein Journal of Organic Chemistry 16: 2937-2947

2020

ISSN/ISBN: 1860-5397
PMID: 33335601
DOI: 10.3762/bjoc.16.243
Accession: 072441032
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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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