RECYCLIZATION OF 3-ARYL-1H-ISOCHROMENE-4-CARBALDEHYDES AS AN EFFECTIVE APPROACH TO THE SYNTHESIS OF FUNCTIONALIZED ISOCOUMARINS AND ISOQUINOLONES

Authors

DOI:

https://doi.org/10.15407/dopovidi2025.01.049

Keywords:

isocoumarins, isochromenone, isoquinolinone, N-nucleophile, recyclization

Abstract

The aim of this study is to investigate the transformation of 3-aryl-1H-isochromene-4-carbaldehydes into 4-aroyl- 1H-isochromen-1-ones and 4-aroylisoquinolin-1(2H)-ones. Refluxing 3-aryl-1H-isochromene-4-carbaldehydes in methanol in the presence of hydrochloric acid efficiently afforded 4-aroyl-1H-isochromen-1-one derivatives with high yields (75—84 %). Furthermore, the reaction of both 3-aryl-1H-isochromene-4-carbaldehydes and the synthesized 4-aroyl-1H-isochromen-1-ones with ammonia as an N-nucleophile in methanol or ethanol led exclusively to the formation of 4-aroylisoquinolin-1(2H)-ones with yields up to 89 %. The synthesized compounds demonstrate significant potential for applications in synthetic organic and medicinal chemistry.

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References

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Published

27.02.2025

How to Cite

Kukushkina, K., & Moskvina, V. (2025). RECYCLIZATION OF 3-ARYL-1H-ISOCHROMENE-4-CARBALDEHYDES AS AN EFFECTIVE APPROACH TO THE SYNTHESIS OF FUNCTIONALIZED ISOCOUMARINS AND ISOQUINOLONES. Reports of the National Academy of Sciences of Ukraine, (1), 49–57. https://doi.org/10.15407/dopovidi2025.01.049

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