Mild Synthesis of Substituted 1,2,5-Oxadiazoles Using 1,1′-Carbonyldiimidazole as a Dehydrating Agent

• DOI: 10.1021/acs.orglett.8b00568
• Publication Date: 2018-03-19T14:36:32Z
• Authors: Andrew J. Neel; Ralph Zhao
• Keywords: 01 natural sciences; 0104 chemical sciences

1,1′-Carbonyldiimidazole was found to induce the formation of a variety 3,4-disubstituted 1,2,5-oxadiazoles (furazans) from corresponding bisoximes at ambient temperature. This method enables these inherently energetic compounds be prepared temperatures well below their decomposition points and with improved functional group compatibility relative prior methods. Conditions were developed that allowed for first high-yielding synthesis chlorofurazans amino counterparts, enabling mild synthetic manipulation heterocycles.