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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

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Date
08/2020
Author
Romo, Pablo
Quiroga, Jairo
Cobo, Justo
Glidewell, Christopher
Keywords
Heterocyclic compound
Synthesis
Indoline
Pyrrolizine
Dipolar cycloaddition
Dispiro compound
NMR spectroscopy
Crystal structure
Molecular conformation
Hydrogen bonding
Supramolecular assembly
QD Chemistry
DAS
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Abstract
The 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.
Citation
Romo , 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/S2053229620009791
Publication
Acta Crystallographica Section C Structural Chemistry
Status
Peer reviewed
DOI
https://doi.org/10.1107/S2053229620009791
ISSN
2053-2296
Type
Journal article
Rights
Copyright © 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.
Description
The 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.
Collections
  • University of St Andrews Research
URI
http://hdl.handle.net/10023/20351

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