000125987 001__ 125987
000125987 005__ 20241125101139.0
000125987 0247_ $$2doi$$a10.3390/ijms24087583
000125987 0248_ $$2sideral$$a133538
000125987 037__ $$aART-2023-133538
000125987 041__ $$aeng
000125987 100__ $$aSierra, S.
000125987 245__ $$aSynthesis of Bis(amino acids) containing the Styryl-cyclobutane Core by Photosensitized [2+2]-Cross-cycloaddition of Allylidene-5(4H)-oxazolones
000125987 260__ $$c2023
000125987 5060_ $$aAccess copy available to the general public$$fUnrestricted
000125987 5203_ $$aThe irradiation of 2-aryl-4-(E-3′-aryl-allylidene)-5(4H)-oxazolones 1 with blue light (456 nm) in the presence of [Ru(bpy)3](BF4)2 (bpy = 2,2′-bipyridine, 5% mol) gives the unstable cyclobutane-bis(oxazolones) 2 by [2+2]-photocycloaddition of two oxazolones 1. Each oxazolone contributes to the formation of 2 with a different C=C bond, one of them reacting through the exocyclic C=C bond, while the other does so through the styryl group. Treatment of unstable cyclobutanes 2 with NaOMe/MeOH produces the oxazolone ring opening reaction, affording stable styryl-cyclobutane bis(amino acids) 3. The reaction starts with formation of the T1 excited state of the photosensitizer 3[Ru*(bpy)3]2+, which reacts with S0 of oxazolones 1 through energy transfer to give the oxazolone T1 state 3(oxa*)-1, which is the reactive species and was characterized by transient absorption spectroscopy. Measurement of the half-life of 3(oxa*)-1 for 1a, 1b and 1d shows large values for 1a and 1b (10–12 μs), while that of 1d is shorter (726 ns). Density functional theory (DFT) modeling displays strong structural differences in the T1 states of the three oxazolones. Moreover, study of the spin density of T1 state 3(oxa*)-1 provides clues to understanding the different reactivity of 4-allylidene-oxazolones described here with respect to the previously reported 4-arylidene-oxazolones.
000125987 536__ $$9info:eu-repo/grantAgreement/ES/MICINN/IJC-2020-044217-I$$9info:eu-repo/grantAgreement/ES/DGA-FSE/E07-20R$$9info:eu-repo/grantAgreement/ES/DGA/E19-20R$$9info:eu-repo/grantAgreement/ES/AEI/PID2019-110441RB-C33$$9info:eu-repo/grantAgreement/ES/AEI/PID2019-106394GB-I00$$9info:eu-repo/grantAgreement/ES/MICINN/PID2019-104379RB-C21-AEI-10.13039-501100011033
000125987 540__ $$9info:eu-repo/semantics/openAccess$$aby$$uhttp://creativecommons.org/licenses/by/3.0/es/
000125987 590__ $$a4.9$$b2023
000125987 592__ $$a1.179$$b2023
000125987 591__ $$aBIOCHEMISTRY & MOLECULAR BIOLOGY$$b66 / 313 = 0.211$$c2023$$dQ1$$eT1
000125987 593__ $$aMedicine (miscellaneous)$$c2023$$dQ1
000125987 591__ $$aCHEMISTRY, MULTIDISCIPLINARY$$b68 / 231 = 0.294$$c2023$$dQ2$$eT1
000125987 593__ $$aPhysical and Theoretical Chemistry$$c2023$$dQ1
000125987 593__ $$aComputer Science Applications$$c2023$$dQ1
000125987 593__ $$aInorganic Chemistry$$c2023$$dQ1
000125987 593__ $$aSpectroscopy$$c2023$$dQ1
000125987 593__ $$aOrganic Chemistry$$c2023$$dQ1
000125987 593__ $$aMolecular Biology$$c2023$$dQ2
000125987 593__ $$aCatalysis$$c2023$$dQ2
000125987 594__ $$a8.1$$b2023
000125987 655_4 $$ainfo:eu-repo/semantics/article$$vinfo:eu-repo/semantics/publishedVersion
000125987 700__ $$aDalmau, D.
000125987 700__ $$0(orcid)0000-0002-0769-7168$$aAlegre-Requena, J. V.
000125987 700__ $$aPop, A.
000125987 700__ $$aSilvestru, C.
000125987 700__ $$aMarín, M. L.
000125987 700__ $$aBoscá, F.
000125987 700__ $$0(orcid)0000-0001-9779-5820$$aUrriolabeitia, E. P.
000125987 773__ $$g24, 8 (2023), 7583 [20 pp.]$$pInt. j. mol. sci.$$tInternational Journal of Molecular Sciences$$x1661-6596
000125987 8564_ $$s4318679$$uhttps://zaguan.unizar.es/record/125987/files/texto_completo.pdf$$yVersión publicada
000125987 8564_ $$s2830625$$uhttps://zaguan.unizar.es/record/125987/files/texto_completo.jpg?subformat=icon$$xicon$$yVersión publicada
000125987 909CO $$ooai:zaguan.unizar.es:125987$$particulos$$pdriver
000125987 951__ $$a2024-11-22-12:02:00
000125987 980__ $$aARTICLE