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...
Saved in:
Published in | Synthesis (Stuttgart) no. 18; pp. 2791 - 2796 |
---|---|
Main Authors | , , , , , |
Format | Journal Article |
Language | English |
Published |
STUTTGART
Thieme Medical Publishers
17.09.2007
|
Subjects | |
Online Access | Get more information |
Cover
Loading…
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 |