Online article for Non-subscribers

Pay per view

Heterocycles has a pay-per-view service for Non-subscribers.
You will be able to directly purchase the full text article through PayPal.
Your purchased Paper can be downloaded after the payment is completed.
An e-mail will be sent the URL to download the paper.
If you have any questions, please contact: purchase@heterocycles.com

Price: ¥ 4,320 (Yen only)
Period: This Article can be accessed for 7 days.

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

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.