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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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.
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Language:English
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Chemistry and Materials Science
Organic Chemistry
Pharmacy
Synthesis
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container_title Chemistry of heterocyclic compounds (New York, N.Y. 1965)
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description 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.
doi_str_mv 10.1007/s10593-020-02671-y
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Organic Chemistry
Pharmacy
Synthesis
title An unexpected synthesis of β-amino-α-mesyl-γ-sultams upon mesylation of hindered α-aminonitriles
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