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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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Diastereoselective synthesis of benzofuran-3(2H)-one-hydantoin dyads_10.1016j.tet.2013.04.111.pdf | 914.62 kB | Adobe PDF |
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