RECYCLIZATION OF 3-ARYL-1H-ISOCHROMENE-4-CARBALDEHYDES AS AN EFFECTIVE APPROACH TO THE SYNTHESIS OF FUNCTIONALIZED ISOCOUMARINS AND ISOQUINOLONES
DOI:
https://doi.org/10.15407/dopovidi2025.01.049Keywords:
isocoumarins, isochromenone, isoquinolinone, N-nucleophile, recyclizationAbstract
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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