Abstract
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.
Räber, J L