Ring Opening of 1-Azabicyclo[1.1.0]butanes with Hydrazoic Acid – a Facile Access to N-Unsubstituted Azetidin-3-Amines

✍ Scribed by Grzegorz Mlostoń; Małgorzata Celeda

• Publisher: John Wiley and Sons
• Year: 2005
• Tongue: German
• Weight: 163 KB
• Volume: 88
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/hlca.200590130

✦ Synopsis

Abstract

Sterically congested 1‐azabicyclo[1.1.0]butanes 1 add hydrazoic acid smoothly at 0–5°, giving 3‐azidoazetidines 2 in good to excellent yields. After hydrogenolysis over Pd/C catalyst, compounds 2 were converted into N‐unsubstituted azetidin‐3‐amines 4. Attempted reduction of 2a with Raney‐Ni led to a mixture of the expected azetidin‐3‐amine 4a and the ring‐enlarged 2,5‐dihydro‐1__H__‐imidazole derivative 5.