邻氨基芳香腈与羰基化合物的反应机理及其产物的骨架结构

doi:10.6023/cjoc201406007

摘要/Abstract

Friedländer反应是合成具有生物活性、光电活性的喹啉衍生物的重要方法. 其典型转化之一——邻氨基芳香腈与羰基化合物的Friedländer缩合在得到经典的转化产物的同时可以得到新骨架产物, 这种新转化自本课题组报道以来已受到国内外学者的诸多关注, 但该转化的新产物骨架结构尚存争议. 本综述概括了该新转化自发现以来国内外的研究进展, 从¹³C NMR, FT-IR, X射线单晶衍射数据等明确了新转化反应得到的产物骨架为喹唑啉酮结构. 完整地提出了该类Friedländer分岔反应的转化机理: 经由分子内的Pinner反应到Dimroth重排的过程存在于邻氨基芳香腈和酮的经典Friedländer反应中(PDF反应).

关键词: 邻氨基芳香腈, 分岔转化, Friedländer转化, 喹唑啉酮, 苯并噁嗪, 产物结构

Friedländer reaction is one of the most important routes to synthesize the quinoline and its derivatives, which possesses excellent bioactivity and photo-electricity activity. Recently, a new skeleton product besides the normal Friedländer quinoline was discovered by the condensation of aromatic o-aminonitrile and carbonyl compounds, and this phenomenon has attracted many researchers, but the skeleton structure of new conversion is debated. Herein, this paper reviews on the development progress of this new kind reaction. According to recent research results, the skeleton structure of new conversion was assigned as quinazolinone, which was confirmed by the ¹³C NMR, FT-IR, and single-crystal X-ray diffraction deterimations. Therefore, this new conversion is abbreviated as PDF conversion, which means a new conversion from Pinner to Dimroth rearrangement in the Friedländer reaction. The total reaction mechanism of o-aminonitrile with carbonyl compound was proposed.

Key words: aromatic o-aminonitrile, divergent conversion, Friedländer conversion, quinazolinone, benzoxazine, product structure

引用此文

杨俊娟, 史大昕, 刘明星, 张立军, 张奇, 李加荣. 邻氨基芳香腈与羰基化合物的反应机理及其产物的骨架结构[J]. 有机化学, 2014, 34(12): 2424-2437.

Yang Junjuan, Shi Daxin, Liu Mingxing, Zhang Lijun, Zhang Qi, Li Jiarong. Structure of the Condensed Product of Aromatic o-Aminonitrile with Carbonyl Compound and Its Mechanism[J]. Chin. J. Org. Chem., 2014, 34(12): 2424-2437.

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