Photoreaction of 2′-chloro-4-R-benzanilide: synthesis of 2-(4-R-phenyl)-1,3-benzoxazole and 9-R-phenanthridin-6(5H)-one (R=H, CH3, CH3O) |
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Authors: | Ahmed M Mayouf Yong-Tae Park |
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Institution: | Department of Chemistry, Kyungpook National University, 702-701, Taegu, South Korea |
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Abstract: | The UV photolysis of 2′-chloro-4-R-benzanilides in acetonitrile solution under nitrogen atmosphere leads to the formation of intramolecular photocyclization products (9-R-phenanthridin-6(5)-one, 20–30%), along with the minor photoreduction, photo-Fries, and intramolecular photosubstitution products. The photoreaction of 2′-chloro-4-R-benzanilide in acetonitrile solution containing 10% of water or aqueous sodium hydroxide however gives 2-(4-R-phenyl)-1,3-benzoxazole as a major product (30%) along with the photoreduction, photo-Fries and intramolecular photocyclization products. |
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Keywords: | 2′-Chloro-4-R-benzanilides Intramolecular photocyclization Intramolecular photosubstitution Solvent and substituent effect |
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