Organobase catalyzed 1,4-conjugate addition of 4-hydroxycoumarin on chalcones: Synthesis, NMR and single-crystal X-ray diffraction studies of novel warfarin analogues
authors Talhi, O; Fernandes, JA; Pinto, DCGA; Paz, FAA; Silva, AMS
nationality International
journal JOURNAL OF MOLECULAR STRUCTURE
author keywords Warfarin analogues; Bicyclo[3.3.1]nonanes; 1,4-Conjugate addition; Organobase catalysis; NMR; X-ray diffraction
keywords DERIVATIVES; ANTICOAGULATION; CONFORMATIONS; THERAPY
abstract The synthesis of a new series of warfarin analogues by convenient organobase catalyzed 1,4-conjugate addition of 4-hydroxycoumarin to chalcone derivatives is described. H-1 NMR spectroscopy evidenced the presence of a predominant acyclic open-form together with the cyclic hemiketal tautomers of the resulting Michael adducts. The acyclic open-form has been unequivocally proved by single-crystal X-ray diffraction analysis. The use of the B ring ortho-hydroxychalcone synthons in this reaction has led to a diastereoselective synthesis of warfarin bicyclo[3.3.1]nonane ketal derivatives. (C) 2015 Elsevier B.V. All rights reserved.
publisher ELSEVIER SCIENCE BV
issn 0022-2860
year published 2015
volume 1094
beginning page 13
ending page 21
digital object identifier (doi) 10.1016/j.molstruc.2015.03.069
web of science category Chemistry, Physical
subject category Chemistry
unique article identifier WOS:000355714800003
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journal impact factor 2.011
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