Photooxidation of 1,4-Dihyropyridines
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概要
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1,4-Dihydropyridines were successfully photooxidized to corresponding pyridines under suitable conditions. The substituents of the dihydropyridines, reaction mediums, and atmospheres affect the course of the reactions. When diethyl 2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate (<B>1a</B>), diethyl 1,4-dihydropyridine-3,5-dicar-boxylate (<B>1b</B>), 2,6-dimethyl-3,5-diacetyl-1,4-dihydropyridine (<B>1c</B>), and 3,5-diacetyl-1,4-dihydropyridine (<B>1d</B>) were irradiated by a super high pressure mercury lamp with filter in ethanol under air or oxygen, corresponding pyridines, diethyl 2,6-dimethylpyridine-3,5-dicarboxylate (<B>2a</B>), diethyl pyridine-3,5-dicarboxylate (<B>2b</B>), 2,6-dimethyl-3,5-diacethylpyridine (<B>2c</B>), and 3,5-diacetylpyridine (<B>2d</B>) were formed in good yields. Irradiation of <B>1a</B>, <B>1c</B>, and <B>1d</B> in acetonitrile afforded <B>2a</B>, <B>2c</B>, and <B>2d</B> irrespective of their atomosphere, oxygen or nitrogen. On the other hand, photolysis of <B>1b</B> by the same lamp and filter in ethanol or acetonitrile in an atmosphere of nitrogen resulted in the formation of photodimer (<B>3</B>) which on irradiation by low pressure mercury lamp in acetonitrile dissociated to <B>1b</B> followed by photooxidation giving <B>2b</B>. Diethyl l-acetyl-1,4-dihydropyridine-3,5-dicarbolxyate (<B>4e</B>) and 1,3,5-triacetyl-1,4-dihydropyridine (<B>4f</B>) afforded <B>2b</B> and <B>2d</B> in fairly good yields when the photolyses were carried out in an atmosphere of air in ethanol or acetonitrile.
- 公益社団法人 日本化学会の論文
著者
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Masuda Hiroaki
Department Of Cardiovascular Medicine Graduate School Of Medicine University Of Tokyo
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Wada Makoto
Department Of Chemistry Faculty Of Integrated Arts And Sciences The University Of Tokushima
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Mitsunobu Oyo
Department Of Chemistry College Of Science And Engineering Aoyama Gakuin University
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Matsumoto Shozo
Department of Chemistry, College of Science and Engineering, Aoyama Gakuin University
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