A study of atypical reaction of methyl -acetate with 3a-substituted bicyclic [beta]-keto-[gamma]-sultams

A number of 2-substituted 4-7-membered cyclic amino acid esters bearing endocyclic amino group were sequentially mesylated and cyclized via the CSIC reaction strategy to give the key precursors 3a-substituted bicyclic isothiazolidin-4-one 1,1-dioxides. Further reaction with methyl (triphenylphosphor...

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Published inChemistry of heterocyclic compounds (New York, N.Y. 1965) Vol. 57; no. 2; p. 207
Main Authors Omelian, Taras V, Iegorov, Pavlo O, Poliudov, Anton O, Dobrydnev, Alexey V, Ostapchuk, Eugeniy N, Volovenko, Yulian M
Format Journal Article
LanguageEnglish
Published Springer 01.02.2021
Subjects
Drug discovery
Sulfonamides
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Summary:A number of 2-substituted 4-7-membered cyclic amino acid esters bearing endocyclic amino group were sequentially mesylated and cyclized via the CSIC reaction strategy to give the key precursors 3a-substituted bicyclic isothiazolidin-4-one 1,1-dioxides. Further reaction with methyl (triphenylphosphoranylidene) acetate afforded the corresponding 3a-substituted 2-[(triphenylphosphonio)acetyl]-perhydro[1,2]thiazoloazahetaryl-3-olate 1,1-dioxides. The nature of the substituent at position 3a plays a crucial role in the reaction direction with this Wittig reagent. Specifically, 3a-unsubstituted counterpart participates in the classical course of the reaction providing the expected prototropic mixture of corresponding esters.
ISSN:0009-3122
1573-8353
DOI:10.1007/s10593-021-02894-7