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

• 津田 喜典

  Faculty of Pharmaceutical Sciences, Kanazawa University

• 津田 喜典

  Faculty Of Pharmaceutical Sciences Kanazawa University

• 佐野 武弘

  Showa College of Pharmaceutical Sciences.

• 堀口 よし江

  昭和薬大

• 津田 喜典

  金沢大薬

• 堀口 よし江

  Showa College of Pharmaceutical Sciences

• 佐野 武弘

  Showa Pharmaceutical Univ. Tokyo Jpn

• 佐野 武弘

  Showa College Of Pharmaceutical Sciences

• 堀口 よし江

  Showa College Of Pharmaceutical Sciences University Of Kanazawa

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