Photodecarboxylative addition of carboxylates to phthalimides: a concise access to biologically active 3-(alkyl and aryl)methylene-1H-isoindolin-1-ones
Hatoum, Fadi, Engler, Jana, Zelmer, Christina, Wissen, Johannes, Motti, Cherie Ann, Lex, Johann, and Oelgemoeller, Michael (2012) Photodecarboxylative addition of carboxylates to phthalimides: a concise access to biologically active 3-(alkyl and aryl)methylene-1H-isoindolin-1-ones. Tetrahedron Letters, 53 (42). pp. 5573-5577.
![[img]](https://researchonline.jcu.edu.au/style/images/fileicons/application_pdf.png) |
PDF (Published Version)
- Published Version
Restricted to Repository staff only |
Abstract
A series of 3-(alkyl and aryl)methyleneisoindolin-1-one derivatives were synthesized in a simple two-step procedure using a recently established photodecarboxylative addition of carboxylates to phthalimides as the key-step. Subsequent acid-catalyzed dehydration and deprotection furnished the desired target compounds with high E-selectivity. The reaction sequence was applied to the synthesis of the known bioactive phenylethylene derivative, AKS-186. Different analogues, including heteroatom-containing isosteres were also synthesized using this approach.
| Item ID: | 23373 |
|---|---|
| Item Type: | Article (Research - C1) |
| ISSN: | 1873-3581 |
| Date Deposited: | 14 Sep 2012 04:18 |
| FoR Codes: | 03 CHEMICAL SCIENCES > 0305 Organic Chemistry > 030503 Organic Chemical Synthesis @ 75% 03 CHEMICAL SCIENCES > 0305 Organic Chemistry > 030505 Physical Organic Chemistry @ 25% |
| SEO Codes: | 97 EXPANDING KNOWLEDGE > 970103 Expanding Knowledge in the Chemical Sciences @ 100% |
| Downloads: |
Total: 5 |
| More Statistics |
Actions (Repository Staff Only)
 |
Item Control Page |