Abstract
A series of 1-substituted isochromanes has been synthesized from the corresponding alkyl 2- acylphenylacetates 3, by reduction and cyclization with a catalytic amount of p-toluenesulfonic acid monohydrate (PTSA), as compounds with potential antitumor activity and N-bearing heterocycle analogues.
Highlights
The biological activity of some isochromane derivatives has provided a great deal of interest in the synthesis
Many isochromanes have been synthesized as intermediates of the synthesis of anxiolytic 2,3-benzodiazepines, which are known as 2-amino-3-(3-hydroxy-5-methylisoxazol-4yl)propionic acid (AMPA) receptor antagonists.[2,3,4]
The hydroxyisochromanes were prepared by saponification of 5-formylmellein,[34] reduction of isocoumarins with hydrides,[35,36] reaction of benzocyclobutenols and aromatic aldehydes in the presence of lithium 2,2,6,6-tetramethylpiperidide,[37] photo-induced hetero- Diels-Alder reaction of 2-methylbenzldehydes,[38] oxidation of 2-(2-hydroxyethyl)-5-isopropylbenzyl alcohol,39 2hydroxymethyl-1-(2’-hydroxyphenyl)naphthalene[40] with non-activated manganese dioxide or pyridinium chlorochromate, or by reaction of an alcohol and triethyl orthoformate catalyzed by aluminum chloride followed by catalytic hydrogenation.[41]
Summary
The biological activity of some isochromane derivatives has provided a great deal of interest in the synthesis.
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