An unexpected synthesis of β-amino-α-mesyl-γ-sultams upon mesylation of hindered α-aminonitriles

We report one-pot procedure for an unexpected synthesis of previously unknown 4-amino-5-methylsulfonyl-2,3-dihydroisothiazole 1,1-dioxides (also called β-amino-α-mesyl-γ-sultams). Thus, the reaction of mesyl chloride with hindered α-aminonitriles is accompanied by the formation of interim N -(1-cyan...

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Bibliographic Details
Published in:Chemistry of heterocyclic compounds (New York, N.Y. 1965) N.Y. 1965), 2020-03, Vol.56 (3), p.386-391
Main Authors: Dyachenko, Maksim S., Dobrydnev, Alexey V., Chuchvera, Yaroslav O., Shishkina, Svitlana V., Volovenko, Yulian M.
Format: Article
Language:English
Subjects:
Chemistry
Chemistry and Materials Science
Organic Chemistry
Pharmacy
Synthesis
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Summary:We report one-pot procedure for an unexpected synthesis of previously unknown 4-amino-5-methylsulfonyl-2,3-dihydroisothiazole 1,1-dioxides (also called β-amino-α-mesyl-γ-sultams). Thus, the reaction of mesyl chloride with hindered α-aminonitriles is accompanied by the formation of interim N -(1-cyanoalkyl)(methylsulfonyl)methanesulfonamides which, in turn, undergo the сarbanion-mediated sulfonate (sulfonamido) intramolecular cyclization reaction yielding β-amino-α-mesyl-γ-sultams. The structure of the title compounds was confirmed by X-ray diffraction study. The proposed mechanistic insights of the reaction are in accordance with the results of additional experiments and literature data.
ISSN:0009-3122
1573-8353
DOI:10.1007/s10593-020-02671-y