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Paper | Special issue | Vol 74, No. 1, 2007, pp.397-409
Published online, 21st September, 2007
DOI: 10.3987/COM-07-S(W)18
A Novel Heterospirocyclic 2H-Azirin-3-amine as Synthon for 3-Aminothiolane-3-carboxlic Acid

Joëlle L. Räber, Kathrin A. Brun, and Heinz Heimgartner*

*Institute of Organic Chemistry, University of Zürich, Winterthurerstrasse 190, CH-8057 Zürich, Switzerland


The heterospirocyclic 2H-azirin-3-amine (9), i.e., N-methyl-N-phenyl-5-thia-1-azaspiro[2.4]hept-1-en-2-amine, was prepared from the commercially available thiolane-3-one (10) via the corresponding 3-carbonitrile (11) and 3-thiocarboxamide (14). This azirine reacted with thiobenzoic acid to give 3-benzoylamino-N-methyl-N-phenylthiolane-3-thiocarboxamide (15). With N-protected valine, the protected dipeptides (16) and (17), which contain a heterocyclic amino acid, were obtained as mixtures of diastereoisomers.