Synthesis of 1,3-Selenazoles and Bis(selenazoles) from Primary Selenocarboxylic Amides and Selenourea

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

doi:10.1055/s-2004-822312

PAPER

Synthesis of 1,3-Selenazoles and Bis(selenazoles) from Primary Selenocarboxylic Amides and Selenourea

Karlheinz Geisler*, Wolf-Diethard Pfeiffer, Andreas Künzler, Harald Below, Ehrenfried Bulka, 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

The reaction of nitriles with P₂Se₅ in the presence of EtOH-H₂O afforded primary selenocarboxylic amides. The cyclization of these compounds with α-halo ketones afforded a variety of functionalized 1,3-selenazoles. The use of P₂Se₅ also allowed the convenient synthesis of selenocarboxylic diamides which were transformed into bis(selenazol-2-yl)alkanes (‘bis-selenazoles’). A practical method for the synthesis of selenourea was developed. This useful small building block was successfully applied to the synthesis of primary 2-amino-1,3-selenazoles.

Key words

cyclizations - heterocycles - nitriles - selenium - amides

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References

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