Synthesis 2004(1): 97-105  
DOI: 10.1055/s-2003-44348
PAPER
© Georg Thieme Verlag Stuttgart · New York

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;
Further Information

Publication History

Received 8 July 2003
Publication Date:
19 November 2003 (online)

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.