Cycloadditions in Syntheses. XXVI. : 1,2-Dihydrocyclobuta[b]-naphthalene-3,8-diones : Synthesis by Photochemical Means and Their Reactions via 2,3-Dimethylene-1,4-dioxo-1,2,3,4-tetrahydronaphthalenes

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概要

• 論文の詳細を見る

• 2-Chloro-1,4-naphthoquinone undergoes photochemical 2+2 addition to alkenes. Elimination of hydrogen chloride from the adducts provides a facile and general synthetic method for 1,2-dihydrocyclobuta[b]naphthalene-3,8-diones. Heating of the latter compounds affords 2,3-dimethylene-1,2,3,4-tetrahydronaphthalene-1,4-diones, which react in situ with alkenes to give the 4+2 adducts. 1-Formyl-1,2-dihydrocyclobuta[b]naphthalene-3,8-dione obtained by the use of the above two-step procedure using acrolein dimethylacetal as the alkene in the first step affords upon heating 1H-naphtho[2,3-c]pyran-2,10-dione via electrocyclization of the corresponding dimethylenecompound. If an enone is used as the alkene in the first step, the addition occurs in a 4+2 manner to give directly 4H-naphtho[2,3-b]pyra-5,10-diones.

• 公益社団法人日本薬学会の論文
• 1986-04-25

著者

• 金子 主税

  Faculty Of Pharmaceutical Sciences Kanazawa University

• 金子 主税

  Pharmaceutical Institute Medical Faculty University Of Tokyo

• 内藤 俊彦

  Faculty of Pharmaceutical Sciences, Kanazawa University

• 巻田 吉彦

  Faculty of Pharmaceutical Sciences, Kanazawa University

• 金子 主税

  Pharmaceutical Institute Tohoku University

• 矢崎 塩美

  Faculty of Pharmaceutical Sciences, Kanazawa University

• 矢崎 塩美

  Faculty Of Pharmaceutical Sciences Kanazawa University

• 巻田 吉彦

  Faculty Of Pharmaceutical Sciences Kanazawa University

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