Diastereoselective synthesis of benzofuran-3(2H)-one-hydantoin dyads
authors Talhi, O; Fernandes, JA; Pinto, DCGA; Paz, FAA; Silva, ASM
nationality International
journal TETRAHEDRON
author keywords Benzofuran-3(2H)-one; Hydantoin; Diastereoselective synthesis; X-ray crystallography; 2D NMR
keywords CYCLIN-DEPENDENT KINASES; INDIRUBIN DERIVATIVES; INHIBITORY-ACTIVITIES; CYTOTOXIC AGENTS; HYBRIDS; DESIGN; INDOLE; POTENT
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.
publisher PERGAMON-ELSEVIER SCIENCE LTD
issn 0040-4020
year published 2013
volume 69
issue 26
beginning page 5413
ending page 5420
digital object identifier (doi) 10.1016/j.tet.2013.04.111
web of science category Chemistry, Organic
subject category Chemistry
unique article identifier WOS:000320295000020
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