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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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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. / Romo, Pablo; Quiroga, Jairo; Cobo, Justo; Glidewell, Christopher.

In: Acta Crystallographica Section C Structural Chemistry, Vol. 76, No. 8, C76, 08.2020.

Research output: Contribution to journalArticlepeer-review

Harvard

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

APA

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, 76(8), [C76]. https://doi.org/10.1107/S2053229620009791

Vancouver

Romo P, Quiroga J, Cobo J, Glidewell C. 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. 2020 Aug;76(8). C76. https://doi.org/10.1107/S2053229620009791

Author

Romo, Pablo ; Quiroga, Jairo ; Cobo, Justo ; Glidewell, Christopher. / 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. In: Acta Crystallographica Section C Structural Chemistry. 2020 ; Vol. 76, No. 8.

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@article{7a883b0602f14b158512ff9f70f93737,
title = "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",
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. ",
keywords = "Heterocyclic compound, Synthesis, Indoline, Pyrrolizine, Dipolar cycloaddition, Dispiro compound, NMR spectroscopy, Crystal structure, Molecular conformation, Hydrogen bonding, Supramolecular assembly",
author = "Pablo Romo and Jairo Quiroga and Justo Cobo and Christopher Glidewell",
note = "The authors thank 'Centro de Instrumentaci{\'o}n Cient{\'i}fico-T{\'e}cnica of Universidad de Ja{\'e}n' for data collection. The authors thank COLCIENCIAS, Universidad del Valle, the Consejer{\'i}a de Innovaci{\'o}n, Ciencia y Empresa (Junta de Andaluc{\'i}a, Spain) and the Universidad de Ja{\'e}n for financial support. JQ thanks the AUIP for a scholarship granted for a stay at the Universidad de Ja{\'e}n. ",
year = "2020",
month = aug,
doi = "10.1107/S2053229620009791",
language = "English",
volume = "76",
journal = "Acta Crystallographica Section C Structural Chemistry",
issn = "2053-2296",
publisher = "International Union of Crystallography",
number = "8",

}

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TY - JOUR

T1 - Regio- and stereospecific assembly of dispiro[indoline-3,3′-pyrrolizine-1′,5′′-thiazolidines] from simple precursors using a one-pot procedure

T2 - synthesis, spectroscopic and structural characterization, and a proposed mechanism of formation

AU - Romo, Pablo

AU - Quiroga, Jairo

AU - Cobo, Justo

AU - Glidewell, Christopher

N1 - 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.

PY - 2020/8

Y1 - 2020/8

N2 - 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.

AB - 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.

KW - Heterocyclic compound

KW - Synthesis

KW - Indoline

KW - Pyrrolizine

KW - Dipolar cycloaddition

KW - Dispiro compound

KW - NMR spectroscopy

KW - Crystal structure

KW - Molecular conformation

KW - Hydrogen bonding

KW - Supramolecular assembly

U2 - 10.1107/S2053229620009791

DO - 10.1107/S2053229620009791

M3 - Article

VL - 76

JO - Acta Crystallographica Section C Structural Chemistry

JF - Acta Crystallographica Section C Structural Chemistry

SN - 2053-2296

IS - 8

M1 - C76

ER -

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