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Synthesis and reactions of some new benzopyranone derivatives with potential biological activities
Author(s) -
ElDesoky ElSayed I.,
AlShihry Shar S.
Publication year - 2008
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570450648
Subject(s) - chemistry , aniline , formylation , yield (engineering) , malononitrile , acetonitrile , derivative (finance) , medicinal chemistry , claisen rearrangement , ethyl cyanoacetate , cyclohexane , organic chemistry , bromide , catalysis , materials science , economics , financial economics , metallurgy
Reaction of visnaginone which derived from the naturally occurring compound “visnagine”, with allyl bromide gave O ‐allyl visnaginone 1 , which underwent Claisen rearrangement to yield 7‐allylbenzofuran 2 derivative. Vilsmeier Haack formylation of 2 afforded our versatile starting compound furochromene‐6‐carboxaldehyde ( 3 ) which was condensed with cyclohexane‐1,3‐dione, indandione, malononitrile or ethyl cyanoacetate to yield the ylidene nicotinonitrile and pyridone derivatives 4,7,10a‐b . Reaction of 3 with aniline or aniline acting on multiple function X‐H (X = NH, O, S) at its ortho position afforded the corresponding anils, imidazolylfurochromene and azepines compounds 11‐17 . On the other hand, oxidation of visnagin afforded chromene‐6‐carboxaldehyde derivative 18 which was condensed with different aryl or (heteroaryl) acetonitrile followed by hydrolysis to give pyrano[3,2‐ g ]chromen‐4,8‐dione derivatives 20a‐d and 22 .