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Synthesis 2010(19): 3358-3362  
DOI: 10.1055/s-0030-1257868
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

1-Acylsemicarbazides by Ring Opening of Iminodiaziridines with Carboxylic Acids: Novel, Expeditious Access to the Azapeptide Motif

Helmut Quast*, Edeltraud Schmitt, Karl-Heinz Ross
Institut für Organische Chemie der Universität Würzburg, Am Hubland, 97074 Würzburg, Germany
Fax: +49(541)8141935; e-Mail: hquast@uni-osnabrueck.de;
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Publication History

Received 11 March 2010
Publication Date:
22 July 2010 (online)

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Abstract

Carboxylic acids react rapidly and quantitatively with iminodiaziridines to afford 1,2,4-trisubstituted 1-acylsemicarbazides in a multistep sequence. In this way, a carboxy group is readily converted into an azapeptide motif. Broad signals in high-field ¹H and ¹³C NMR spectra recorded for the products are indicative of dynamic processes.

Key words

azapeptides - heterocycles - hydrolysis - ring-opening - semicarbazides

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