Synthesis of 4,5-disubstituted-3-trihalomethylisothiazoles

Herein, we describe the synthesis of 4,5-disubstituted-3-trihalomethylisothiazoles from trihaloacetonitriles and 2-cyanothioacetamides or 2-ethoxycarbonylthioacetamides. The reactivity of the necessary trihaloacetonitriles has a significant impact on the observed reaction pathways. Reactions with CF...

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Bibliographic Details
Published inTetrahedron letters Vol. 50; no. 52; pp. 7286 - 7287
Main Authors Zawistoski, Michael P., Decker, Shannon M., Griffith, David A.
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier Ltd 30.12.2009
Elsevier
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ISOTHIAZOLES
ISOTHIAZOLO<5,4-D>PYRIMIDINES
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Summary:Herein, we describe the synthesis of 4,5-disubstituted-3-trihalomethylisothiazoles from trihaloacetonitriles and 2-cyanothioacetamides or 2-ethoxycarbonylthioacetamides. The reactivity of the necessary trihaloacetonitriles has a significant impact on the observed reaction pathways. Reactions with CF 3CN require an oxidant to mediate cyclization, while CCl 3CN functions as both the reactant and oxidant.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2009.10.051