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
Anamimoghadam, Ommid, Mumtaz, Saira, Nietsch, Anke, Saya, Gaetano, Motti, Cherie A., Wang, Jun, Junk, Peter C., Qureshi, Ashfaq Mahmood, and Oelgemöller, Michael (2017) 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. Beilstein Journal of Organic Chemistry, 13. pp. 2833-2841.
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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.
| Item ID: | 51861 |
|---|---|
| Item Type: | Article (Research - C1) |
| ISSN: | 1860-5397 |
| Keywords: | anesthetics; arylmethylenedihydroisoindolinones; photochemistry; photodecarboxylation; phthalimide |
| Additional Information: | This is an Open Access article under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/4.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. |
| Funders: | Australian Research Council (ARC), Higher Education Commission Pakistan |
| Projects and Grants: | ARC DP130100794 |
| Date Deposited: | 08 Jan 2018 01:48 |
| FoR Codes: | 34 CHEMICAL SCIENCES > 3405 Organic chemistry > 340503 Organic chemical synthesis @ 70% 34 CHEMICAL SCIENCES > 3405 Organic chemistry > 340505 Physical organic chemistry @ 30% |
| SEO Codes: | 97 EXPANDING KNOWLEDGE > 970103 Expanding Knowledge in the Chemical Sciences @ 100% |
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