Please use this identifier to cite or link to this item: http://hdl.handle.net/10995/103196
Title: Regioselective synthesis of heterocyclic N-sulfonyl amidines from heteroaromatic thioamides and sulfonyl azides
Authors: Ilkin, V.
Berseneva, V.
Beryozkina, T.
Glukhareva, T.
Dianova, L.
Dehaen, W.
Seliverstova, E.
Bakulev, V.
Issue Date: 2020
Publisher: Beilstein-Institut Zur Forderung der Chemischen Wissenschaften
Citation: Regioselective synthesis of heterocyclic N-sulfonyl amidines from heteroaromatic thioamides and sulfonyl azides / V. Ilkin, V. Berseneva, T. Beryozkina, et al. — DOI 10.3762/BJOC.16.243 // Beilstein Journal of Organic Chemistry. — 2020. — Vol. 16. — P. 2937-2947.
Abstract: 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. © 2020 Ilkin et al.
Keywords: 1,2,3-TRIAZOLES
AMIDINES
DIMROTH REARRANGEMENT
ISOXAZOLES
SULFONYL THIAZOLES
THIOAMIDES
URI: http://hdl.handle.net/10995/103196
Access: info:eu-repo/semantics/openAccess
SCOPUS ID: 85098581931
PURE ID: 20413665
ad633c7e-cdcc-45bf-bab3-0e52eb488a92
ISSN: 18605397
DOI: 10.3762/BJOC.16.243
metadata.dc.description.sponsorship: The authors thank the Russian Science Foundation (project №18-13-00161).
RSCF project card: 18-13-00161
Appears in Collections:Научные публикации, проиндексированные в SCOPUS и WoS CC

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