Photoaddition of ketones to imidazoles,thiazoles, isothiazoles and isoxazoles. Synthesis of their oxetanes |
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Authors: | Tatsuhiko Nakano,Wilma Rodrí guez,Severina Z. De Roche,Jos M. Larrauri,Carlos Rivas,Carmen P rez |
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Affiliation: | Tatsuhiko Nakano,Wilma Rodríguez,Severina Z. De Roche,José M. Larrauri,Carlos Rivas,Carmen Pérez |
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Abstract: | Imidazole itself did not undergo photoaddition reactions with ketones. However, irradiation of 1-acetyl and 1-benzoylimidazole, and 1,1-carbonyldiimidazole with benzophenone yielded oxetanes. On irradiation with carbonyl compounds, 1,2-dimethylimidazole and 1-benzylimidazole did not give oxetanes but a hydroxyaryl or hydroxyalkyl derivative. Thiazole itself did not yield any photoaddition product, but 2,4-dimethylthiazole afforded oxetanes on irradiation with benzophenone and with 3-benzoylpyridine. Irradiation of 2,4-dimethylthiazole with acetophenone led to the formation of a dimeric material. On irradiation with benzophenone, 4-methylisothiazole did not yield an oxetane but rather a hydroxyphenyl derivative. 3,5-Dimethylisoxazole on irradiation with benzophenone and with 3-benzoylpyridine gave oxetanes. Irradiation of 4,5-dimethylisoxazole yielded similarly an oxetane with benzophenone |
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