The Neber approach to 2-(Tetrazol-5-yl)-2H-Azirines

• Author(s): Cardoso, Ana Lúcia ; Gimeno, Lourdes ; Lemos, A. ; Palacios, Francisco ; Melo, Teresa M. V. D. Pinho e
• Date: 2013
• Persistent ID: http://hdl.handle.net/10400.1/5688
• Origin: Sapientia - Universidade do Algarve
• Document Type: Journal article
• Language: English
• Contributor(s): Sapientia

Description

The synthesis of 2-(tetrazol-5-yl)-2H azirines is reported for the first time. Using the Neber approach, β-ketoxime-1H-tetrazoles were converted into the target 2Hazirines bearing phenyl, furan-2-yl, thiophen-2-yl, or pyrrol-2-yl substituents at C-3. It was demonstrated that the alkaloidmediated Neber reaction allows the asymmetric synthesis of 2-(tetrazol-5-yl)-2H-azirines.