膦亚胺叶立德在杂环合成中的应用  

Application of iminophosphorane in heterocyclic synthesis

作　　者：丁明武[1] 

机构地区：[1]农药与化学生物学教育部重点实验室华中师范大学,武汉430079

出　　处：《中国科学：化学》2010年第7期869-877,共9页SCIENTIA SINICA Chimica

基　　金：国家自然科学基金(20772041,20102001);教育部科学技术研究重点项目(107082)资助

摘　　要：总结了我们课题组应用膦亚胺叶立德的氮杂Wittig反应合成氮杂环的研究工作.我们发展了一种应用α-酯基膦亚胺与异氰酸酯(或二硫化碳)、亲核试剂的连续成环反应,合成咪唑啉酮及唑类杂环的新方法.应用β-酯基膦亚胺与异氰酸酯(或二硫化碳)、亲核试剂的连续成环反应,则可制备(稠合的)喹唑啉酮和嘧啶酮类杂环.而应用β-炔基膦亚胺与异氰酸酯、亲核试剂在银离子催化下的连续成环反应,可得到吲哚类杂环.最近我们课题组又初步将膦亚胺叶立德应用于串联的Ugi和Passerini后修饰反应中,合成了多取代苯并嗪和喹唑啉类杂环化合物.Recent work of our group on the synthesis of heterocycles via aza-Wittig reaction of iminophosphorane was reviewed.We have developed a new efficient synthesis of various imidazolones or oxazoles by utilizing a consecutive cyclization of α-ethoxycarbonyl iminophosphorane,isocynate（or carbon disulfide） and various nucleophilic reagents.New derivatives of（fused） quinazolinones and pyrimidinones were prepared from the tandem reaction of β-ethoxycarbonyl iminophosphorane,isocynate（or carbon disulfide） and various nucleophilic reagents.Indole derivatives were also obtained in good yields from the sequential reaction of β-phenylethynyl iminophosphorane,isocynate and various nucleophilic reagents in the presence of a catalytic amount of Ag＋.Recently the iminophosphorane was applied in post-condensation modifications of Ugi and Passerini reactions to prepare multisubstituted benzoxazines and quinazolines.

关 键 词：膦亚胺 氮杂WITTIG反应 叶立德 杂环 

分 类 号：O621.3[理学—有机化学]