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dc.contributor.authorRomo, Pablo
dc.contributor.authorQuiroga, Jairo
dc.contributor.authorCobo, Justo
dc.contributor.authorGlidewell, Christopher
dc.date.accessioned2020-07-28T14:30:02Z
dc.date.available2020-07-28T14:30:02Z
dc.date.issued2020-08
dc.identifier.citationRomo , P , Quiroga , J , Cobo , J & Glidewell , C 2020 , ' Regio- and stereospecific assembly of dispiro[indoline-3,3′-pyrrolizine-1′,5′′-thiazolidines] from simple precursors using a one-pot procedure : synthesis, spectroscopic and structural characterization, and a proposed mechanism of formation ' , Acta Crystallographica Section C Structural Chemistry , vol. 76 , no. 8 , C76 . https://doi.org/10.1107/S2053229620009791en
dc.identifier.issn2053-2296
dc.identifier.otherPURE: 269246406
dc.identifier.otherPURE UUID: 7a883b06-02f1-4b15-8512-ff9f70f93737
dc.identifier.otherScopus: 85089170344
dc.identifier.otherWOS: 000581048400009
dc.identifier.urihttps://hdl.handle.net/10023/20351
dc.descriptionThe authors thank 'Centro de Instrumentación Científico-Técnica of Universidad de Jaén' for data collection. The authors thank COLCIENCIAS, Universidad del Valle, the Consejería de Innovación, Ciencia y Empresa (Junta de Andalucía, Spain) and the Universidad de Jaén for financial support. JQ thanks the AUIP for a scholarship granted for a stay at the Universidad de Jaén.en
dc.description.abstractThe synthesis and characterization of three new di­spiro­[indoline-3,3′-pyrrolizine-1′,5′′-thia­zolidine] com­pounds are reported, together with the crystal structures of two of them. (3RS,1′SR,2′SR,7a′SR)-2′-(4-Chloro­phen­yl)-1-hexyl-2′′-sulfanyl­idene-5′,6′,7′,7a′-tetra­hydro-2′H-di­spiro­[indoline-3,3′-pyrrolizine-1′,5′′-thia­zolidine]-2,4′′-dione, C28H30ClN3O2S2, (I), (3RS,1′SR,2′SR,7a′SR)-2′-(4-chloro­phen­yl)-1-benzyl-5-methyl-2′′-sulfanyl­idene-5′,6′,7′,7a′-tetra­hydro-2′H-di­spiro­[in­doline-3,3′-pyrrolizine-1′,5′′-thia­zolidine]-2,4′′-dione, C30H26ClN3O2S2, (II), and (3RS,1′SR,2′SR,7a′SR)-2′-(4-chloro­phen­yl)-5-fluoro-2′′-sulfanyl­idene-5′,6′,7′,7a′-tetra­hydro-2′H-di­spiro­[indoline-3,3′-pyrrolizine-1′,5′′-thia­zolidine]-2,4′′-dione, C22H17ClFN3O2S2, (III), were each isolated as a single regioisomer using a one-pot reaction involving L -proline, a substituted isatin and (Z)-5-(4-chloro­benzyl­idene)-2-sulfanyl­idene­thia­zolidin-4-one [5-(4-chloro­benzyl­idene)rhodanine]. The com­positions of (I)–(III) were established by elemental analysis, com­plemented by high-resolution mass spectrometry in the case of (I); their constitutions, including the definition of the regiochemistry, were established using NMR spectroscopy, and the relative configurations at the four stereogenic centres were established using single-crystal X-ray structure analysis. A possible reaction mechanism for the formation of (I)–(III) is proposed, based on the detailed stereochemistry. The mol­ecules of (I) are linked into simple chains by a single N—H⋯N hydrogen bond, those of (II) are linked into a chain of rings by a combination of N—H⋯O and C—H⋯S=C hydrogen bonds, and those of (III) are linked into sheets by a combination of N—H⋯N and N—H⋯S=C hydrogen bonds.
dc.format.extent7
dc.language.isoeng
dc.relation.ispartofActa Crystallographica Section C Structural Chemistryen
dc.rightsCopyright © 2020 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.subjectHeterocyclic compounden
dc.subjectSynthesisen
dc.subjectIndolineen
dc.subjectPyrrolizineen
dc.subjectDipolar cycloadditionen
dc.subjectDispiro compounden
dc.subjectNMR spectroscopyen
dc.subjectCrystal structureen
dc.subjectMolecular conformationen
dc.subjectHydrogen bondingen
dc.subjectSupramolecular assemblyen
dc.subjectQD Chemistryen
dc.subjectDASen
dc.subject.lccQDen
dc.titleRegio- and stereospecific assembly of dispiro[indoline-3,3′-pyrrolizine-1′,5′′-thiazolidines] from simple precursors using a one-pot procedure : synthesis, spectroscopic and structural characterization, and a proposed mechanism of formationen
dc.typeJournal articleen
dc.description.versionPublisher PDFen
dc.contributor.institutionUniversity of St Andrews. School of Chemistryen
dc.identifier.doihttps://doi.org/10.1107/S2053229620009791
dc.description.statusPeer revieweden


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