Structure of the Condensed Product of Aromatic o-Aminonitrile with Carbonyl Compound and Its Mechanism

doi:10.6023/cjoc201406007

Abstract

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

Cite this article

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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