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A Flexible Synthetic Approach to Fluorescent Chromeno[4,3-b]pyridines and Pyrano[3,2-c]chromenes from Electron-Deficient 3-Vinylchromones
ChemPlusChem ( IF 3.0 ) Pub Date : 2021-08-19 , DOI: 10.1002/cplu.202100296
Nikita M Chernov 1 , Roman V Shutov 1 , Nadezhda Yu Sipkina 2 , Maxim N Krivchun 3 , Igor P Yakovlev 1
Affiliation  

We report a flexible approach to the synthesis of phenanthrene-like heterocycles through organocatalytic ANRORC (Addition of the Nucleophile, Ring Opening, and Ring Closure) reaction of electron-deficient 3-vinylchromones with cyanoacetamide. Addition of highly basic DBU (1,8-diazabicyclo[5.4.0]undec-7-ene) or tetramethylguanidine (TMG) at 80 °C leads to chromeno[4,3-b]pyridines in good yields, whereas Et3N at 20 °C made it possible to obtain the less accessible pyrano[3,2-c]chromenes and their 2-imines. The synthesis proceeds in mild conditions (EtOH, 20–80 °C), is versatile and applicable for a wide scope of reactants. The obtained compounds show bright fluorescence in the range 460–595 nm with high quantum yields (up to 0.84) in various solvents (MeCN, DMSO, EtOH, H2O).

中文翻译:


从缺电子 3-乙烯基色酮中合成荧光色并[4,3-b]吡啶和吡喃并[3,2-c]色烯的灵活合成方法



我们报告了一种通过缺电子 3-乙烯基色酮与氰基乙酰胺的有机催化 ANRORC(亲核试剂加成、开环和闭环)反应合成菲类杂环的灵活方法。在 80 °C 下添加高碱性 DBU(1,8-二氮杂双环[5.4.0]十一碳-7-烯)或四甲基胍 (TMG) 会以良好的产率生成色并[4,3- b ]吡啶,而 Et 3 N在 20 °C 下,可以获得不易获得的吡喃并[3,2- c ]色烯及其 2-亚胺。该合成在温和条件(EtOH,20–80 °C)下进行,用途广泛,适用于多种反应物。所得化合物在各种溶剂(MeCN、DMSO、EtOH、H 2 O)中显示出460-595 nm范围内的明亮荧光,并具有高量子产率(高达0.84)。
更新日期:2021-09-02
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