Universität zu Köln

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

Full text not available from this repository.

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:	Creators Email ORCID ORCID Put Code Hatoum, Fadi UNSPECIFIED UNSPECIFIED UNSPECIFIED Engler, Jana UNSPECIFIED UNSPECIFIED UNSPECIFIED Zelmer, Christina UNSPECIFIED UNSPECIFIED UNSPECIFIED Wissen, Johannes UNSPECIFIED UNSPECIFIED UNSPECIFIED Motti, Cherie Ann UNSPECIFIED UNSPECIFIED UNSPECIFIED Lex, Johann UNSPECIFIED UNSPECIFIED UNSPECIFIED Oelgemoeller, Michael UNSPECIFIED UNSPECIFIED UNSPECIFIED
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:	Keywords Language ALPHA-KETO CARBOXYLATES; ONE-POT SYNTHESIS; PHOTOSENSITIZED DECARBOXYLATION; ISOINDOLINONE DERIVATIVES; STEREOSELECTIVE-SYNTHESIS; SUBSTITUTED CARBOXYLATES; N-ALKYLPHTHALIMIDES; INHIBITORY-ACTIVITY; ACIDS; BIOISOSTERISM Multiple languages Chemistry, Organic Multiple languages
URI:	http://kups.ub.uni-koeln.de/id/eprint/48096