Synthesis and Reactivity of 2-Acyl-1,3-selenazoles

Karlheinz Geisler; Andreas Künzler; Harald Below; Ehrenfried Bulka; Wolf-Diethard Pfeiffer; Peter Langer

doi:10.1055/s-2003-44348

PAPER

Synthesis and Reactivity of 2-Acyl-1,3-selenazoles

Karlheinz Geisler*, Andreas Künzler, Harald Below, Ehrenfried Bulka, Wolf-Diethard Pfeiffer, Peter Langer*
Institut für Chemie und Biochemie, Ernst-Moritz-Arndt-Universität Greifswald, Soldmannstr. 16, 17487 Greifswald, Germany
Fax: +49(3834)864346; e-Mail: peter.langer@uni-greifswald.de;

Abstract

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Abstract

2-Acyl-1,3-selenazoles were prepared in two steps from α-bromoketones and seleno amides. The base mediated fragmentation of these compounds afforded 2-unsubstituted 1,3-selenazoles. The reaction of 2-acyl-1,3-selenazoles with hydroxylamine hydrochloride afforded oximes which were transformed into 2-carbamoyl-1,3-selenazoles by a regioselective Beckmann rearrangement.

Key words

cyclization - fragmentation - selenium heterocycles - rearrangement - 1,3-selenazoles

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References

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