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Novel rearrangement of 1,3-benzo(naphtho)dioxin-4(1)-ones under Vilsmeier-Haack reagent
Monatshefte für Chemie - Chemical Monthly ( IF 1.7 ) Pub Date : 2021-01-23 , DOI: 10.1007/s00706-020-02733-z Oleg K. Farat , Anton V. Kovtun , Svetlana A. Varenichenko , Aleksander V. Mazepa , Victor I. Markov
中文翻译:
Vilsmeier-Haack试剂下1,3-苯并(萘)二恶英-4(1)-的新型重排
更新日期:2021-01-24
Monatshefte für Chemie - Chemical Monthly ( IF 1.7 ) Pub Date : 2021-01-23 , DOI: 10.1007/s00706-020-02733-z Oleg K. Farat , Anton V. Kovtun , Svetlana A. Varenichenko , Aleksander V. Mazepa , Victor I. Markov
Polyfunctional derivatives of xanthenes and benzoxanthenes in the form of organic perchlorates have been obtained by the interaction of 1,3-benzo(naphtho)dioxin-4(1)-ones with the Vilsmeier-Haack reagent at 110 °C for 5 h. The rearrangement has occurred as an electrophilic triggered recyclization due to the geminal arrangement of oxygen atoms in the six-membered ring as well as the presence of a lactone group in the structure of the starting 1,3-benzo(naphtho)dioxin-4(1)-ones.
Graphic abstract
中文翻译:
Vilsmeier-Haack试剂下1,3-苯并(萘)二恶英-4(1)-的新型重排
通过在110°C下将1,3-苯并(萘)二恶英-4(1)-1与Vilsmeier-Haack试剂相互作用5 h,获得了有机高氯酸盐形式的黄嘌呤和苯并氧杂蒽的多官能衍生物。由于六元环中氧原子的双键排列以及起始的1,3-苯并(萘)二恶英-4(内酯基团)中内酯基团的存在,重排反应作为亲电触发的再循环发生。 1)-个。