Dioxopyrroline. L. Skeletal Rearrangements of 7-Vinyl-7-trimethylsilyloxy-5-ethoxycarbonyl-1-phenyl-2-azabicyclo[3.2.0]heptane-3,4-diones under Thermal, Basic, and Acidic Conditions

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概要

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• The oxyvinylcyclobutanes (2), photoadducts of the dioxopyrrolines (1) to trimethylsilyloxybutadienes, undergo two different types of skeletal rearrangements depending on the reaction conditions. Thermolysis of 2 caused expansion of the cyclobutane ring by a 1,3-shift of the C_1-C_7 bond toward the vinyl group, giving rise to the hydroindoles (3) in moderate yields. This 1,3-shift was enormously accelerated when an alkoxide was generated by the action of tetrabutylammonium fluoride (TBAF) on trimethylsilyloxyvinylcyclobutanes. Thus, 2a-d, on treatment with TBAF at -30℃, provided hydroindole derivatives in good yields, though in some cases (2a, b) accompanied with by-products (10). This demonstrates that the [2+2] photoannulation of dioxopyrroline, when coupled with the anionic 1,3-shift, provides an efficient synthetic route to functionalized hydroindoles. Under acidic conditions, the oxyvinylcyclobutanes(2) rearranged to give exclusively the 2-azatricyclo[4.3.0.0^<4,9>]nonanes (10), whose formation was rationalized in terms of the intramolecular Prins-type cyclization with concomitant expansion of the cyclobutane ring by 1,2-shift of the C_1-C_7 bond toward the vinyl group.

• 公益社団法人日本薬学会の論文
• 1992-01-25

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.

• 津田 喜典

  金沢大薬

• 戸田 潤

  Showa College of Pharmaceutical Sciences

• 佐野 武弘

  昭和薬科大学

• 佐野 武弘

  Showa Pharmaceutical Univ. Tokyo Jpn

• 佐野 武弘

  Showa College Of Pharmaceutical Sciences

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