A stereoselective synthesis of symmetrical and unsymmetrical bibenzo[e][1,3]oxazine-2,2 '-dione derivatives induced by low-valent titanium reagent

作者：Dou, Guo-Lan; Sun, Fang; Shi, Da-Qing^*

来源：Tetrahedron, 2012, 68(24): 4852-4859.

DOI：10.1016/j.tet.2012.03.122

• Bibenzo[e][1,3]oxazine-2,2 '-dione
• Low-valent titanium reagent
• Synthesis

A series of symmetrical and unsymmetrical bibenzo[e][1,3]oxazine-2,2'-dione derivatives were synthesized by the reaction of various o-hydroxy Schiff bases and triphosgene induced by low-valent titanium reagent (TiCl4/Sm). A variety of substrates can participate in the process with good yields. The present method provides a useful preparation of 3,3',4,4'-tetrahydro-4,4'-bibenzo[e][1,3]oxazine-2,2'-dione derivatives, which cannot be prepared otherwise. The mechanistic course of the reaction suggests the involvement of reduction, coupling, and cyclization by one-pot.

• 出版日期2012-6-17
• 单位苏州大学; 中国矿业大学（北京）