The photodecarboxylative addition of carboxylates to phthalimides as a key-step in the synthesis of biologically active 3-arylmethylene-2,3-dihydro-1H-isoindolin-1-ones
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Media type:
E-Article
Title:
The photodecarboxylative addition of carboxylates to phthalimides as a key-step in the synthesis of biologically active 3-arylmethylene-2,3-dihydro-1H-isoindolin-1-ones
Published in:
Beilstein Journal of Organic Chemistry, 13 (2017), Seite 2833-2841
Language:
English
DOI:
10.3762/bjoc.13.275
ISSN:
1860-5397
Origination:
Footnote:
Description:
<jats:p>The synthesis of various 3-arylmethylene-2,3-dihydro-1<jats:italic>H</jats:italic>-isoindolin-1-ones was realized following a simple three-step process. The protocol utilized the photodecarboxylative addition of readily available carboxylates to <jats:italic>N</jats:italic>-(bromoalkyl)phthalimides as a versatile and efficient key step. The initially obtained hydroxyphthalimidines were readily converted to the desired <jats:italic>N</jats:italic>-diaminoalkylated 3-arylmethylene-2,3-dihydro-1<jats:italic>H</jats:italic>-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.</jats:p>