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 Lett., 53 (42). S. 5573 - 5578. OXFORD: PERGAMON-ELSEVIER SCIENCE LTD. ISSN 0040-4039

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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. (C) 2012 Elsevier Ltd. All rights reserved.

Item Type: Journal Article
Creators:
CreatorsEmailORCIDORCID Put Code
Hatoum, FadiUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Engler, JanaUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Zelmer, ChristinaUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Wissen, JohannesUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Motti, Cherie AnnUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Lex, JohannUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
Oelgemoeller, MichaelUNSPECIFIEDUNSPECIFIEDUNSPECIFIED
URN: urn:nbn:de:hbz:38-480968
DOI: 10.1016/j.tetlet.2012.07.142
Journal or Publication Title: Tetrahedron Lett.
Volume: 53
Number: 42
Page Range: S. 5573 - 5578
Date: 2012
Publisher: PERGAMON-ELSEVIER SCIENCE LTD
Place of Publication: OXFORD
ISSN: 0040-4039
Language: English
Faculty: Unspecified
Divisions: Unspecified
Subjects: no entry
Uncontrolled Keywords:
KeywordsLanguage
ALPHA-KETO CARBOXYLATES; ONE-POT SYNTHESIS; PHOTOSENSITIZED DECARBOXYLATION; ISOINDOLINONE DERIVATIVES; STEREOSELECTIVE-SYNTHESIS; SUBSTITUTED CARBOXYLATES; N-ALKYLPHTHALIMIDES; INHIBITORY-ACTIVITY; ACIDS; BIOISOSTERISMMultiple languages
Chemistry, OrganicMultiple languages
URI: http://kups.ub.uni-koeln.de/id/eprint/48096

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