State Key Laboratory of Chemical Resource Engineering, Department of Organic Chemistry, College of Chemistry, Beijing University of Chemical Technology, Beijing 100029, P. R. China.
China Tianchen Engineering Corporation, Tianjin 300400, China.
Org Biomol Chem. 2021 Sep 15;19(35):7678-7689. doi: 10.1039/d1ob01359a.
-(2,2-Diphenylvinyl)-β-oxoamides are both the structural moiety of biologically active compounds and important synthetic intermediates. Structurally diverse -(2,2-diphenylvinyl)-β-oxoamides are prepared efficiently from 2-diazo-1,3-dicarbonyl compounds and -alkyl-2,2-diphenylaziridines an electrophilic ring opening reaction under two different reaction conditions of reflux and microwave irradiation. 2-Diazo-1,3-dicarbonyl compounds undergo the Wolff rearrangement under heating to generate α-oxoketenes, which electrophilically react with -alkylaziridines to directly produce structurally diverse -(2,2-diphenylvinyl)-β-oxoamides in good to excellent yields under microwave irradiation. Microwave irradiation accelerates the reaction obviously and efficiently. Both 2-diazo-1,3-diketones and alkyl 2-diazo-3-oxoalkanoates work well. The reaction is catalyst-free and highly atom economical, involves only loss of nitrogen and does not require additives. The products are useful synthons for the convenient preparation of multisubstituted β-lactam derivatives.
-(2,2-二苯基乙烯基)-β-氧代酰胺既是具有生物活性的化合物的结构部分，也是重要的合成中间体。通过两种不同的反应条件回流和微波辐射下的亲电环开反应，从 2-重氮-1,3-二羰基化合物和-α-烷基-2,2-二苯基氮丙啶高效制备结构多样的-(2,2-二苯基乙烯基)-β-氧代酰胺。2-重氮-1,3-二羰基化合物在加热下发生Wolff 重排生成α-氧代烯酮，其在微波辐射下与-α-烷基氮丙啶亲电反应，直接生成结构多样的-(2,2-二苯基乙烯基)-β-氧代酰胺，产率良好至优秀。微波辐射明显且有效地加速了反应。2-重氮-1,3-二酮和α-烷基 2-重氮-3-氧代烷酸酯都能很好地反应。该反应无需催化剂，具有很高的原子经济性，仅损失氮，不需要添加剂。这些产物是方便制备多取代β-内酰胺衍生物的有用的合成子。
