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Synthesis of 4,4‐Disubstituted 1,2‐Thiazinane‐5‐one 1,1‐Dioxides via the CSIC [≠] Reaction Strategy
Author(s) -
Dyachenko Maksim S.,
Kochetkov Artem O.,
Dobrydnev Alexey V.,
Milokhov Demyd S.,
Shishkina Svitlana V.,
Konovalova Irina S.,
Omelchenko Irina V.,
Volovenko Yulian M.
Publication year - 2020
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.202001243
Subject(s) - sodium hydride , carbanion , chemistry , alkylation , intramolecular force , methyl iodide , iodide , sulfonate , medicinal chemistry , chloride , hydride , alkyl , sodium , stereochemistry , organic chemistry , catalysis , metal
A series of sp 3 ‐enriched 2,2‐disubstituted 1,2‐thiazinane‐5‐one 1,1‐dioxides (including spirocyclic derivatives) has been synthesized through the CSIC [Carbanion mediated Sulfonate (Sulfonamido) Intramolecular Cyclization] reaction strategy. In particular, 2,2‐disubstituted alkyl 3‐aminopropanoates were subsequently sulfonylated with mesyl chloride followed by alkylation with methyl iodide to give the key precursor 2,2‐disubstituted methyl 3‐(methylsulfonamido)propanoates. The latter were treated with sodium hydride and underwent the intramolecular sulfa‐Dieckmann cyclization yielding the target 4,4‐disubstituted 1,2‐thiazinane‐5‐one 1,1‐dioxides (so‐called β‐keto‐δ‐sultams). The structure of the target compounds was confirmed by an X‐ray diffraction study.