One-pot synthesis of substituted isothiazol-3(2H)-ones: Intramolecular annulation of alpha-carbamoyl ketene-S,S-acetals via PIFA-Mediated N-S bond formation

A facile and efficient synthetic route towards; highly substituted isothiazol-3(2H)-ones 2 from readily available U.-carbamoyl ketene-S,S-acetals 1 is presented. The key step features the formation of an N-acylnitrenium ion, generated from the oxidization of substituted amides with the hypervalent i...

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Bibliographic Details
Published inSynthesis (Stuttgart) no. 18; pp. 2791 - 2796
Main Authors Huang, Jie, Lu, Yumei, Qiu, Baofu, Liang, Yongjiu, Li, Nan, Dong, Dewen
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 17.09.2007
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
amidation
PRACTICAL SYNTHESIS
STRATEGY
cyclization
ACYLNITRENIUM IONS
alpha-carbamoyl ketene-S,S-acetals
trifluoroacetic acid
FACILE SYNTHESIS
1,2-BENZISOTHIAZOLE DERIVATIVES
CHEMISTRY
POLYVALENT IODINE
hypervalent iodine reagent
INHIBITORS
isothiazol-3(2H)-ones
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Summary:A facile and efficient synthetic route towards; highly substituted isothiazol-3(2H)-ones 2 from readily available U.-carbamoyl ketene-S,S-acetals 1 is presented. The key step features the formation of an N-acylnitrenium ion, generated from the oxidization of substituted amides with the hypervalent iodine reagent phenyliodine(III) bis(trifluoroacetate) (PIFA), and its succeeding intramolecular amidation to form a new N-S bond affording the title compounds.
ISSN:0039-7881
1437-210X
DOI:10.1055/s-2007-983875