000069752 001__ 69752 000069752 005__ 20190709135616.0 000069752 0247_ $$2doi$$a10.1039/c7ra09995a 000069752 0248_ $$2sideral$$a104774 000069752 037__ $$aART-2017-104774 000069752 041__ $$aeng 000069752 100__ $$aMaiuolo, L. 000069752 245__ $$aNitrones and nucleobase-containing spiro-isoxazolidines derived from isatin and indanone: Solvent-free microwave-assisted stereoselective synthesis and theoretical calculations 000069752 260__ $$c2017 000069752 5060_ $$aAccess copy available to the general public$$fUnrestricted 000069752 5203_ $$aThe spiro-oxindoles have found wide application because of their antiviral properties. However, in the literature few examples of synthesis of their precursors, oxindole-nitrones, are reported. In this paper, we initially present a rapid and efficient synthetic approach to ketonitrones by solvent-free microwave-assisted reaction between isatin or indanone derivatives and various hydroxylamines. The synthetic protocol is facile, clean, fast, high-yielding and stereoselective. Then, we explored the possibility to synthesize nucleobase-containing spiro-isoxazolidines with isatin and indanone nuclei by solvent-free MW-assisted 1, 3-dipolar cycloaddition, obtaining good results in yields (74-85%), and regio- and diastereoselectivity. Theoretical calculations were done to analyze the difference of reactivity of isatin and indanone derivatives with hydroxylamines. 000069752 536__ $$9info:eu-repo/grantAgreement/ES/DGA/E10$$9info:eu-repo/grantAgreement/ES/MINECO-FEDER/CTQ2016-76155-R 000069752 540__ $$9info:eu-repo/semantics/openAccess$$aby-nc$$uhttp://creativecommons.org/licenses/by-nc/3.0/es/ 000069752 590__ $$a2.936$$b2017 000069752 591__ $$aCHEMISTRY, MULTIDISCIPLINARY$$b71 / 171 = 0.415$$c2017$$dQ2$$eT2 000069752 592__ $$a0.863$$b2017 000069752 593__ $$aChemistry (miscellaneous)$$c2017$$dQ1 000069752 593__ $$aChemical Engineering (miscellaneous)$$c2017$$dQ1 000069752 655_4 $$ainfo:eu-repo/semantics/article$$vinfo:eu-repo/semantics/publishedVersion 000069752 700__ $$0(orcid)0000-0002-2202-3460$$aMerino, P.$$uUniversidad de Zaragoza 000069752 700__ $$aAlgieri, V. 000069752 700__ $$aNardi, M. 000069752 700__ $$aDi Gioia, M.L. 000069752 700__ $$aRusso, B. 000069752 700__ $$0(orcid)0000-0001-8355-2289$$aDelso, I.$$uUniversidad de Zaragoza 000069752 700__ $$aTallarida, M.A. 000069752 700__ $$aDe Nino, A. 000069752 7102_ $$12013$$2765$$aUniversidad de Zaragoza$$bDpto. Química Orgánica$$cÁrea Química Orgánica 000069752 773__ $$g7, 77 (2017), 48980-48988$$pRSC ADVANCES$$tRSC Advances$$x2046-2069 000069752 8564_ $$s461939$$uhttps://zaguan.unizar.es/record/69752/files/texto_completo.pdf$$yVersión publicada 000069752 8564_ $$s112472$$uhttps://zaguan.unizar.es/record/69752/files/texto_completo.jpg?subformat=icon$$xicon$$yVersión publicada 000069752 909CO $$ooai:zaguan.unizar.es:69752$$particulos$$pdriver 000069752 951__ $$a2019-07-09-12:25:39 000069752 980__ $$aARTICLE