Publication Repository

Photodecarboxylative addition of carboxylates to phthalimides: a concise access to biologically active 3-(alkyl and aryl)methylene-1H-isoindolin-1-ones

Show simple item record

dc.contributor University Of Cologne
dc.contributor Inst Organ Chem
dc.contributor Ctr Biodiscovery & Mol Dev Therapeut Bmdt
dc.contributor Biomol Anal Facil
dc.contributor James Cook Univ
dc.contributor James Cook University
dc.contributor Sch Pharm & Mol Sci
dc.contributor Dublin City University
dc.contributor Sch Chem Sci
dc.contributor Australian Institute Of Marine Science
dc.contributor Dublin City Univ
dc.contributor Univ Cologne
dc.contributor Australian Inst Marine Sci
dc.contributor Australian Institute Of Marine Science (aims) en
dc.contributor.author OELGEMOELLER, MICHAEL
dc.contributor.author HATOUM, FADI
dc.contributor.author ENGLER, JANA
dc.contributor.author ZELMER, CHRISTINA
dc.contributor.author WISSEN, JOHANNES
dc.contributor.author MOTTI, CHERIE ANN
dc.contributor.author LEX, JOHANN
dc.date.accessioned 2013-02-28T06:49:56Z
dc.date.accessioned 2013-02-28T06:49:56Z
dc.date.accessioned 2017-03-21T01:20:06Z
dc.date.accessioned 2018-11-01T03:25:00Z
dc.date.available 2017-03-21T01:20:06Z
dc.date.available 2013-02-28T06:49:56Z
dc.date.available 2013-02-28T06:49:56Z
dc.date.available 2018-11-01T03:25:00Z
dc.date.issued 2012-10-17
dc.identifier 9261 en
dc.identifier.citation Hatoum F, Engler J, Zelmer C, Wissen J, Motti CA, Lex J and Oelgemoller M (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: 5573-5577. en
dc.identifier.issn 0040-4039
dc.identifier.uri http://epubs.aims.gov.au/11068/9261
dc.description Link to abstract/full text - http://www.sciencedirect.com/science/article/pii/S0040403912013913 en
dc.description.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.
dc.description.sponsorship This research was financially supported by Science Foundation Ireland (SFI, 07/RFP/CHEF817 and 06/RFP/CHO028) and James Cook University (JCU-CRIG 2011). The authors thank Assoc-Prof. Bruce Bowden and Dr. Murray Davies (JCU) for technical assistance.
dc.description.uri http://www.sciencedirect.com/science/article/pii/S0040403912013913 en
dc.language English
dc.language en en
dc.relation.ispartof Tetrahedron Letters - pages: 53: 5573-5577 en
dc.relation.ispartof Null
dc.subject One-pot Synthesis
dc.subject Drug Design
dc.subject Chemistry
dc.subject Phthalimide
dc.subject Chemistry, Organic
dc.subject Photodecarboxylation
dc.subject Stereoselective-synthesis
dc.subject Photoaddition
dc.subject Photochemistry
dc.subject Substituted N-alkylphthalimides
dc.subject Alpha-keto Carboxylates
dc.subject Isoindolinone Derivatives
dc.subject Acids
dc.subject Possessing Inhibitory-activity
dc.subject Analog (u-46619)-induced Vasoconstriction
dc.subject Photoinduced Electron Transfer
dc.subject Decarboxylation Reactions
dc.title Photodecarboxylative addition of carboxylates to phthalimides: a concise access to biologically active 3-(alkyl and aryl)methylene-1H-isoindolin-1-ones
dc.type journal article en
dc.identifier.doi 10.1016/j.tetlet.2012.07.142
dc.identifier.wos WOS:000309436300001


Files in this item

Files Size Format View

There are no files associated with this item.

This item appears in the following Collection(s)

Show simple item record

Search Publication


Browse

My Account