Please use this identifier to cite or link to this item: http://hdl.handle.net/10773/19479
Title: Diastereoselective synthesis of benzofuran-3(2H)-one-hydantoin dyads
Author: Talhi, Oualid
Fernandes, Jose A.
Pinto, Diana C. G. A.
Almeida Paz, Filipe A.
Silva, Artur S. M.
Keywords: CYCLIN-DEPENDENT KINASES
INDIRUBIN DERIVATIVES
INHIBITORY-ACTIVITIES
CYTOTOXIC AGENTS
HYBRIDS
DESIGN
INDOLE
POTENT
Issue Date: 2013
Publisher: PERGAMON-ELSEVIER SCIENCE LTD
Abstract: a-convenient diastereoselective rearrangement of the racemic (R/S)-spirolchroman-2,4'-imidazolidine]-2',4,5'-triones 3a-c into (2'R,5S)- and (2'S,5R)-5-(3-oxo-2,3-dihydrobenzofuran-2-yl)imidazolidine-2,4-diones 4a-c under alkali conditions is described. The obtained sigma bridged benzofuran-3(2H)-one-hydantoin dyads 4a-c are subsequently transformed into pi conjugated benzofuran-3(2H)-one-hydantoin dyads 5a-c by a diastereoselective dehydrogenation using I-2 (catalytic)/DMSO system to predominantly yield the (Z)-isomer. The novel single and double bonded benzofuran-3(2H)-one-hydantoin conjugate structures 4a-c and 5a-c were unambiguously elucidated by single-crystal X-ray diffraction and 2D NMR techniques allowing an in-depth stereochemical and mechanistic discussions. (C) 2013 Elsevier Ltd. All rights reserved.
Peer review: yes
URI: http://hdl.handle.net/10773/19479
DOI: 10.1016/j.tet.2013.04.111
ISSN: 0040-4020
Publisher Version: 10.1016/j.tet.2013.04.111
Appears in Collections:CICECO - Artigos

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