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Synthesis of Novel 3 a ‐Substituted Tetrahydro‐1 H ‐1λ 6 ‐pyrrolo[1,2‐ b ]isothiazole‐1,1,3(2 H )‐triones through the CSIC Reaction
Author(s) -
Omelian Taras V.,
Dobrydnev Alexey V.,
Ostapchuk Eugeniy N.,
Volovenko Yulian M.
Publication year - 2019
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201900650
Subject(s) - isothiazole , carbanion , chemistry , medicinal chemistry , sulfonate , condensation , intramolecular force , stereochemistry , organic chemistry , sodium , physics , thermodynamics
We report a strategy for the construction of tetrahydro‐1 H ‐1λ 6 ‐pyrrolo[1,2‐ b ]isothiazole‐1,1,3(2 H )‐triones bearing the substituents at the 5‐ and/or 3a‐positions. To this purpose, a range of 2‐substituted and 2,4‐disubstituted methyl 2‐pyrrolidinecarboxylates were sulfonylated with methanesulfonyl chloride and the resulting sulfonamides were subjected to sulfa‐Dieckmann condensation through the CSIC (Carbanion mediated Sulfonate (Sulfonamido) Intramolecular Cyclization) reaction to give the desired 1λ 6 ‐isothiazolidine‐1,1,4‐triones. All the precursors, as well as target compounds, could be synthesized in a multigram scale following the general protocols.