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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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.
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
Acta Crystallographica Section C Structural Chemistry
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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.
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