Photoinduced Annulation of N-Phenylbenzamides for the Synthesis of Phenanthridin-6(5H)-Ones,Advanced Synthesis & Catalysis

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Photoinduced Annulation of N-Phenylbenzamides for the Synthesis of Phenanthridin-6(5H)-Ones
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2022-02-15 , DOI: 10.1002/adsc.202101389
Nana Wang ₁ , Ding Wang ₁ , Yun He ₂ , Jin Xi ₁ , Tao Wang ₁ , Yong Liang ₃ , Zunting Zhang ₁

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A general concise method for the synthesis phenanthridin-6(5H)-ones via photoinduced intramolecular annulation of N-phenylbenzamides was developed. Under argon atmosphere and room temperature, phenanthridin-6(5H)-ones were obtained via irradiation N-phenylbenzamides with a 280 nm UV lamp in the presence of methanesulfonic acid in toluene. The mechanism is illustrated and believed to proceed in the order of amides tautomerization, 6π-electric cyclization, [1,5]-H shift, amide-imidine tautomerization, keto-enol tautomerism and evolution hydrogen.

中文翻译：

N-苯基苯甲酰胺的光诱导环化合成 Phenothridin-6(5H)-Ones

开发了一种通过光诱导N-苯基苯甲酰胺分子内环化合成菲啶-6(5 H )-ones的通用简明方法。在氩气和室温下，在甲苯中甲磺酸存在下，通过用 280 nm 紫外灯照射N-苯基苯甲酰胺，得到菲啶-6(5 H )-酮。该机理被说明并认为按照酰胺互变异构、6π-电环化、[1,5]-H 位移、酰胺-亚胺互变异构、酮-烯醇互变异构和放氢的顺序进行。

更新日期：2022-02-15

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