Photochemical method for preparation of benzo[a]pyrano[3,2-c]phenazin-4-ones from quinoxalines with 4-pyranone unit

IF 2 3区化学 Q2 CHEMISTRY, ORGANIC

Journal of Heterocyclic Chemistry Pub Date : 2024-06-22 DOI:10.1002/jhet.4861

Dmitry V. Tsyganov, Andrey N. Komogortsev, Valeriya G. Melekhina, Artem N. Fakhrutdinov, Boris V. Lichitsky

引用次数: 0

Abstract

Photochemical properties of terarylenes with quinoxalines bridge unit and allomaltol fragment was investigated. We have demonstrated that starting compounds with hydroxyl group in 3-hydroxy-4-pyranone substituent does not undergo any photoinduced transformations. Wherein, conversion to methoxy derivatives allows one to realize photochemical 6π-electrocyclization for considered quinoxalines. Based on data of x-ray analysis the observed difference in reactivity is connected with the presence of hydrogen bond in hydroxyl derivatives. As a result of carried out research photochemical approach to novel benzo[a]pyrano[3,2-c]phenazin-4-ones was implemented.

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从带有 4-吡喃酮单元的喹喔啉制备苯并[a]吡喃并[3,2-c]吩嗪-4-酮的光化学方法

我们研究了带有喹喔啉桥单元和异麦芽酮醇片段的萜烯类化合物的光化学特性。我们已经证明，3-羟基-4-吡喃酮取代基中含有羟基的起始化合物不会发生任何光诱导转化。在这种情况下，转化为甲氧基衍生物可以使考虑的喹喔啉类化合物实现光化学 6π 电环化。根据 X 射线分析数据，观察到的反应性差异与羟基衍生物中存在氢键有关。作为研究成果，我们采用光化学方法制备了新型苯并[a]吡喃并[3,2-c]酚嗪-4-酮。

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来源期刊

Journal of Heterocyclic Chemistry 化学-有机化学

CiteScore

5.20

自引率

4.20%

发文量

177

审稿时长

3.9 months

期刊介绍： The Journal of Heterocyclic Chemistry is interested in publishing research on all aspects of heterocyclic chemistry, especially development and application of efficient synthetic methodologies and strategies for the synthesis of various heterocyclic compounds. In addition, Journal of Heterocyclic Chemistry promotes research in other areas that contribute to heterocyclic synthesis/application, such as synthesis design, reaction techniques, flow chemistry and continuous processing, multiphase catalysis, green chemistry, catalyst immobilization and recycling.