A Deoxygenative [4+1] Annulation Involving N-Acyldiazenes for an Efficient Synthesis of 2,2,5-Trisubstituted 1,3,4-Oxadiazole Derivatives

作者：Zhou, Rong^*; Han, Ling; Zhang, Honghui; Liu, Rongfang^*; Li, Ruifeng

来源：Advanced Synthesis & Catalysis, 2017, 359(22): 3977-3982.

DOI：10.1002/adsc.201700935

• [4+1] annulation
• N-acyldiazenes
• alpha-dicarbonyl compounds
• 1,3,4-oxadiazoles
• phosphines

An unprecedented and highly efficient tris(dimethylamino)phosphine [P(NMe2)(3)]-mediated deoxygenative [4 + 1] annulation of N-acyldiazenes with alpha-dicarbonyl compounds such as isatins, -keto esters, and alpha-diketones is reported. The annulation reactions proceed smoothly under mild conditions to deliver a broad range of 2,2,5-trisubstituted 1,3,4-oxadiazole derivatives in moderate to excellent yields from readily available starting materials. It represents the first realization of the [4+1] annulation mode involving N-acyldiazenes to construct five-membered heterocycles.

• 出版日期2017-11-23
• 单位太原理工大学