Photodecarboxylative addition of carboxylates to phthalimides: a concise access to biologically active 3-(alkyl and aryl)methylene-1H-isoindolin-1-ones
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...
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| Veröffentlicht in: | Tetrahedron letters 2012-10, Vol.53 (42), p.5573-5577 |
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| creator | Hatoum, Fadi Engler, Jana Zelmer, Christina Wißen, Johannes Motti, Cherie Ann Lex, Johann Oelgemöller, Michael |
| description | 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. |
| doi_str_mv | 10.1016/j.tetlet.2012.07.142 |
| format | Article |
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| fulltext | fulltext |
| identifier | ISSN: 0040-4039 |
| ispartof | Tetrahedron letters, 2012-10, Vol.53 (42), p.5573-5577 |
| issn | 0040-4039 1873-3581 |
| language | eng |
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| source | ScienceDirect Journals (5 years ago - present) |
| subjects | Biocompatibility Carboxylates Dehydration Derivatives Photoaddition Photochemistry Photodecarboxylation Photoinduced electron transfer Phthalimide Phthalimides Sequences Synthesis Tetrahedrons |
| title | Photodecarboxylative addition of carboxylates to phthalimides: a concise access to biologically active 3-(alkyl and aryl)methylene-1H-isoindolin-1-ones |
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