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Synthesis 2004(6): 875-884
DOI: 10.1055/s-2004-822312
DOI: 10.1055/s-2004-822312
PAPER
© Georg Thieme Verlag Stuttgart · New York
Synthesis of 1,3-Selenazoles and Bis(selenazoles) from Primary Selenocarboxylic Amides and Selenourea
Weitere Informationen
Received
13 October 2003
Publikationsdatum:
15. März 2004 (online)
Publikationsverlauf
Publikationsdatum:
15. März 2004 (online)
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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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