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.

[img]
Preview
PDF (Published Version) - Published Version
Available under License Creative Commons Attribution.

Download (1MB) | Preview
View at Publisher Website: http://dx.doi.org/10.3762/bjoc.13.275
 
9


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 (Refereed Research - C1)
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.

ISSN: 1860-5397
Funders: Australian Research Council (ARC), Higher Education Commission Pakistan
Projects and Grants: ARC DP130100794
Date Deposited: 08 Jan 2018 01:48
FoR Codes: 03 CHEMICAL SCIENCES > 0305 Organic Chemistry > 030503 Organic Chemical Synthesis @ 70%
03 CHEMICAL SCIENCES > 0305 Organic Chemistry > 030505 Physical Organic Chemistry @ 30%
SEO Codes: 97 EXPANDING KNOWLEDGE > 970103 Expanding Knowledge in the Chemical Sciences @ 100%
Downloads: Total: 9
Last 12 Months: 1
More Statistics

Actions (Repository Staff Only)

Item Control Page Item Control Page