Efficient Fluoride-Mediated
Synthesis of 5-Amino-Substituted Isothiazoles

Yuri S. Zubenko; Vladimir I. Potkin

doi:10.1055/s-0029-1216844

PAPER

Efficient Fluoride-Mediated Synthesis of 5-Amino-Substituted Isothiazoles

Yuri S. Zubenko, Vladimir I. Potkin*
Institute of Physical Organic Chemistry, National Academy of Sciences of Belarus, 13 Surganova Str., 220072 Minsk, Belarus
Fax: +375(17)2841679; e-Mail: potkin@ifoch.bas-net.by;

Abstract

All articles of this category

Abstract

Fluoride-mediated nucleophilic substitution reactions of tert-butyl 4,5-dichloroisothiazole-3-carboxylate with various amines occur under mild conditions yielding 5-(alkylamino)isothiazoles in moderate to high yields.

Key words

isothiazole - fluoride - substitution - amine

Full Text

References

<A NAME="RZ03909SS-1">1</A> Beebe JS. Jani JP. Knauth E. Goodwin P. Higdon C. Rossi AM. Emerson E. Finkelstein M. Floyd E. Harriman S. Atherton J. Hillerman S. Soderstrom C. Kou K. Gant T. Noe MC. Foster B. Rastinejad F. Marx MA. Schaeffer T. Whalen PM. Roberts WG. Cancer Res. 2003, 63: 7301

<A NAME="RZ03909SS-2">2</A> Abdellaoui H. Varaprasad CVNS. Barawkar D. Chakravarty S. Maderna A. Tam R. Chen H. Allan M. Wu JZ. Appleby T. Yan S. Zhang W. Lang S. Yao N. Hamatake R. Hong Z. Bioorg. Med. Chem. Lett. 2006, 16: 5561

<A NAME="RZ03909SS-3">3</A> Lippa B. Morris J. Corbett M. Kwan TA. Noe MC. Snow SL. Gant TG. Mangiaracina M. Coffey HA. Foster B. Knauth EA. Wessel MD. Bioorg. Med. Chem. Lett. 2006, 16: 3444

<A NAME="RZ03909SS-4">4</A> Potkin VI. Zubenko YS. Petkevich SK. Russ. J. Org. Chem. 2008, 44: 1038

<A NAME="RZ03909SS-5">5</A> Bürli RW. Ge Y. White S. Baird EE. Touami SM. Taylor M. Kaizerman JA. Moser HE. Bioorg. Med. Chem. Lett. 2002, 12: 2591

<A NAME="RZ03909SS-6">6</A> Clarck JH. Chem. Rev. 1980, 80: 429

<A NAME="RZ03909SS-7">7</A> Sawyer JS. Schmittling EA. Palkowitz JA. Smith WJ. J. Org. Chem. 1998, 63: 6338

<A NAME="RZ03909SS-8">8</A> Shavnya A. Sakya SM. Minich ML. Rast B. DeMello KL. Jaynes BH. Tetrahedron Lett. 2005, 46: 6887

<A NAME="RZ03909SS-9">9</A> Nechai NI. Dikusar EA. Potkin VI. Kaberdin RV. Russ. J. Org. Chem. 2004, 40: 1009