Journal
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
Volume 13, Issue -, Pages 2833-2841Publisher
BEILSTEIN-INSTITUT
DOI: 10.3762/bjoc.13.275
Keywords
anesthetics; arylmethylenedihydroisoindolinones; photochemistry; photodecarboxylation; phthalimide
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Funding
- Australian Research Council (ARC) [DP130100794]
- Higher Education Commission Pakistan under International Research Support Initiative Program
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The synthesis of various 3-arylmethylene-2,3-dihydro-1H-isoindolin-1-ones was realized following a simple three-step process. The protocol utilized the photodecarboxylative addition of readily available carboxylates to N-(bromoalkyl) phthalimides as a versatile and efficient key step. The initially obtained hydroxyphthalimidines were readily converted to the desired N-diaminoalkylated 3-arylmethylene-2,3-dihydro-1H-isoindolin-1-ones via acid-catalyzed dehydration and subsequent nucleophilic substitution with the corresponding secondary amines. The procedure was successfully applied to the synthesis of known local anesthetics (AL-12, AL-12B and AL-5) in their neutral forms.
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