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dc.contributor.authorRomo, Pablo E.
dc.contributor.authorQuiroga, Jairo
dc.contributor.authorCobo, Justo
dc.contributor.authorGlidewell, Christopher
dc.date.accessioned2021-08-06T12:30:02Z
dc.date.available2021-08-06T12:30:02Z
dc.date.issued2021-09
dc.identifier.citationRomo , P E , Quiroga , J , Cobo , J & Glidewell , C 2021 , ' Synthesis and spectroscopic and structural characterization of spiro[indoline-3,3′-indolizine]s formed by 1,3-dipolar cycloadditions between isatins, pipecolic acid and an electron-deficient alkene ' , Acta Crystallographica Section C Structural Chemistry , vol. 77 , no. Part 9 , C77 . https://doi.org/10.1107/S2053229621007142en
dc.identifier.issn2053-2296
dc.identifier.otherPURE: 275335186
dc.identifier.otherPURE UUID: 48601d1d-9e1e-4375-8e41-7cfb23949f67
dc.identifier.otherWOS: 000693640200001
dc.identifier.urihttp://hdl.handle.net/10023/23733
dc.descriptionThe authors thank the Centro de Instrumentación Cientifico-Técnica of the Universidad de Jaén (UJA) and its staff for the data collection, and thank COLCIENCIAS, the Universidad del Valle, the Universidad de Jaén and the Consejería de Economía, Innovación, Ciencia y Empleo (Junta de Andalucía, Spain) for financial support.en
dc.description.abstractFive new spiro­[indoline-3,3′-indolizine]s have been synthesized with high regio- and stereo­specificity in one-pot three-com­ponent reactions between a sub­sti­tuted indole-2,3-dione, (S)-pipecolic acid and trans-3-benzoyl­acrylic acid, and subsequently characterized using a combination of elemental analysis, IR and 1H and 13C NMR spectroscopy, mass spectrometry and crystal structure analysis. (1′SR,2′SR,3RS,8a′RS)-2′-Benzoyl-5-fluoro-2-oxo-1′,5′,6′,7′,8′,8a′-hexa­hydro-2′H-spiro­[indoline-3,3′-indolizine]-1′-carb­oxy­lic acid, C23H21FN2O4, (I), and (1′SR,2′SR,3RS,8a′RS)-2′-benzoyl-5-methyl-2-oxo-1′,5′,6′,7′,8′,8a′-hexa­hy­dro-2′H-spiro[indoline-3,3′-indolizine]-1′-carb­oxy­lic acid, C24H24N2O4, (II), are isomorphous, as are (1′SR,2′SR,3RS,8a′RS)-2′-benzoyl-1-methyl-2-oxo-1′,5′,6′,7′,8′,8a′-hexa­hydro-2′H-spiro­[indoline-3,3′-indolizine]-1′-carb­oxy­lic acid, C24H24N2O4, (III), and (1′SR,2′SR,3RS,8a′RS)-2′-benzoyl-5-chloro-1-methyl-2-oxo-1′,5′,6′,7′,8′,8a′-hexa­hydro-2′H-spiro­[indoline-3,3′-indolizine]-1′-carb­oxy­lic acid, C24H23ClN2O4, (IV). Within each isomorphous pair, the spiro ring systems show some conformational differences. In each of (I) and (II), the mol­ecules are linked into com­plex sheets by a combination of four types of hydrogen bond, and in each of (III) and (IV), a combination of O—H⋯O and C—H⋯π(arene) hydrogen bonds links the mol­ecules to form a chain of centrosymmetric rings. In (1′SR,2′SR,3RS,8a′RS)-2′-benzoyl-1-hexyl-2-oxo-1′,5′,6′,7′,8′,8a′-hexa­hydro-2′H-spiro­[indoline-3,3′-indolizine]-1′-carb­oxy­lic acid, C29H34N2O4, (V), a combination of five hydrogen bonds links the mol­ecules into sheets of alternating R22(16) and R66(46) rings. A mechanism is proposed for the formation of com­pounds (I)–(V) and some com­parisons with related structures are made.
dc.language.isoeng
dc.relation.ispartofActa Crystallographica Section C Structural Chemistryen
dc.rightsCopyright © The Author(s). This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.en
dc.subjectSynthesisen
dc.subjectHeterocycleen
dc.subjectspiro[- indoline-3,30-indolizine]en
dc.subjectNMR spectroscopyen
dc.subjectReaction mechanismen
dc.subjectCrystal structureen
dc.subjectStereochemistryen
dc.subjectMolecular conformationen
dc.subjectSupramolecular assemblyen
dc.subjectQD Chemistryen
dc.subjectDASen
dc.subject.lccQDen
dc.titleSynthesis and spectroscopic and structural characterization of spiro[indoline-3,3′-indolizine]s formed by 1,3-dipolar cycloadditions between isatins, pipecolic acid and an electron-deficient alkeneen
dc.typeJournal articleen
dc.description.versionPublisher PDFen
dc.contributor.institutionUniversity of St Andrews.School of Chemistryen
dc.identifier.doihttps://doi.org/10.1107/S2053229621007142
dc.description.statusPeer revieweden


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