Synthesis of New 4,4a-Dihydroxanthones via [4+2]-Cycloaddition Reaction

We report a flexible approach to the synthesis of phenanthrene-like heterocycles through organocatalytic AN-RORC (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 Et 3 N 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, H 2 O).

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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

Chernov

Shutov

Sipkina

et al. 2021

ChemPlusChem

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Synthesis of β-vinyl-substituted 4H-chromenes and [4+2] cycloaddition reactions involving them

Семенова

Osipov

Krasnikov

et al. 2023

Chem Heterocycl Comp

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Synthesis of 4,4a-Dihydroxanthone Derivatives Containing Ester and Nitrile Groups

2022

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Synthesis of New 4,4a-Dihydroxanthones via [4+2]-Cycloaddition Reaction

Cited by 3 publications

References 15 publications

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

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

Synthesis of β-vinyl-substituted 4H-chromenes and [4+2] cycloaddition reactions involving them

Synthesis of 4,4a-Dihydroxanthone Derivatives Containing Ester and Nitrile Groups

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