Dioxopyrrolines. XLIX. Synthesis of Azatropolones via Photocycloaddition of 5-Aryl-4-ethoxycarbonyl-1H-pyrrole-2,3-diones to Acetylenes and Ethylenes
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概要
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The first synthesis of derivatives of azatropolone, a new nitrogen heterocycle, and some of their chemical properties are described. Two routes to the azatropolone skeletone were developed; one is the photocycloaddition of dioxopyrrolines 1 to acetylenes followed by thermolysis or photolysis of the resulting cyclobutenes 2 to give the azatropolones 7 or 8,and the other is the ring expansion reaction of the cyclobutanes 5 obtained by the photocycloaddition of 1 to olefins followed by 2,3-dichloro-5,6-dicyano-1,4-benzoquinone dehydrogenation of the resulting dihydroazepines 16 to give the azatropolones 7.The azatropolone rapidly consumed diazomethane; thus 7 gave the 3-O-methylazatropolones 18,while 8 gave mixtures of 3-O-methyl-19 and 2-O-methylazatropolones 20. The position of methylation was proved by the unambiguous synthesis of 18 and of 2-O-ethyl derivatives 24 from 16. The azatropolones 7 and 8,when treated with a protonic solvent, readily underwent a ring contraction reaction giving rise to the pyridine-2-carboxylates 29 and 30,respectively, thus demonstrating that the azatropolone nucleus has a strongly electrophilic character.
- 公益社団法人日本薬学会の論文
- 1990-12-25
著者
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津田 喜典
Faculty of Pharmaceutical Sciences, Kanazawa University
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津田 喜典
Faculty Of Pharmaceutical Sciences Kanazawa University
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佐野 武弘
Showa College of Pharmaceutical Sciences.
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堀口 よし江
昭和薬大
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津田 喜典
金沢大薬
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堀口 よし江
Showa College of Pharmaceutical Sciences
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佐野 武弘
Showa Pharmaceutical Univ. Tokyo Jpn
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佐野 武弘
Showa College Of Pharmaceutical Sciences
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堀口 よし江
Showa College Of Pharmaceutical Sciences University Of Kanazawa
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