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

Journal Publication ResearchOnline@JCU
Anamimoghadam, Ommid;Mumtaz, Saira;Nietsch, Anke;Saya, Gaetano;Motti, Cherie A.;Wang, Jun;Junk, Peter C.;Qureshi, Ashfaq Mahmood;Oelgemöller, Michael
Peter Junk
Abstract

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.

Journal

Beilstein Journal of Organic Chemistry

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Volume

13

ISBN/ISSN

1860-5397

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Pages Count

9

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Publisher

Beilstein-Institut

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DOI

10.3762/bjoc.13.275