A Flexible Synthetic Approach to Fluorescent Chromeno[4,3-b]pyridines and Pyrano[3,2-c]chromenes from Electron-Deficient 3-Vinylchromones,ChemPlusChem

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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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