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4-Styrylquinolines from cyclocondensation reactions between (2-aminophenyl)chalcones and 1,3-diketones: crystal structures and regiochemistry

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4-Styrylquinolines from cyclocondensation reactions between (2-aminophenyl)chalcones and 1,3-diketones : crystal structures and regiochemistry. / Rodríguez, Diego; Guerrero, Sergio Andrés; Palma, Alirio; Cobo, Justo; Glidewell, Christopher.

In: Acta Crystallographica Section C Structural Chemistry, Vol. 76, No. 9, 01.09.2020.

Research output: Contribution to journalArticlepeer-review

Harvard

Rodríguez, D, Guerrero, SA, Palma, A, Cobo, J & Glidewell, C 2020, '4-Styrylquinolines from cyclocondensation reactions between (2-aminophenyl)chalcones and 1,3-diketones: crystal structures and regiochemistry', Acta Crystallographica Section C Structural Chemistry, vol. 76, no. 9. https://doi.org/10.1107/S2053229620010803

APA

Rodríguez, D., Guerrero, S. A., Palma, A., Cobo, J., & Glidewell, C. (2020). 4-Styrylquinolines from cyclocondensation reactions between (2-aminophenyl)chalcones and 1,3-diketones: crystal structures and regiochemistry. Acta Crystallographica Section C Structural Chemistry, 76(9). https://doi.org/10.1107/S2053229620010803

Vancouver

Rodríguez D, Guerrero SA, Palma A, Cobo J, Glidewell C. 4-Styrylquinolines from cyclocondensation reactions between (2-aminophenyl)chalcones and 1,3-diketones: crystal structures and regiochemistry. Acta Crystallographica Section C Structural Chemistry. 2020 Sep 1;76(9). https://doi.org/10.1107/S2053229620010803

Author

Rodríguez, Diego ; Guerrero, Sergio Andrés ; Palma, Alirio ; Cobo, Justo ; Glidewell, Christopher. / 4-Styrylquinolines from cyclocondensation reactions between (2-aminophenyl)chalcones and 1,3-diketones : crystal structures and regiochemistry. In: Acta Crystallographica Section C Structural Chemistry. 2020 ; Vol. 76, No. 9.

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@article{30437bc8ef3f4cafa140421090e1651c,
title = "4-Styrylquinolines from cyclocondensation reactions between (2-aminophenyl)chalcones and 1,3-diketones: crystal structures and regiochemistry",
abstract = "Structures are reported for two matched sets of substituted 4-styryl­quino­lines which were prepared by the formation of the heterocyclic ring in cyclo­condensation reactions between 1-(2-amino­phen­yl)-3-aryl­prop-2-en-1-ones with 1,3-dicarbonyl com­pounds. (E)-3-Acetyl-4-[2-(4-meth­oxy­phen­yl)ethen­yl]-2-methyl­quino­line, C21H19NO2, (I), (E)-3-acetyl-4-[2-(4-bromo­phen­yl)ethen­yl]-2-methyl­quino­line, C20H16BrNO, (II), and (E)-3-acetyl-2-methyl-4-{2-[4-(tri­fluoro­meth­yl)phen­yl]ethen­yl}quino­line, C21H16F3NO, (III), are isomorphous and in each structure the mol­ecules are linked by a single C—H...O hydrogen bond to form C(6) chains. In (I), but not in (II) or (III), this is augmented by a C—H...π(arene) hydrogen bond to form a chain of rings; hence, (I)–(III) are not strictly isostructural. By contrast with (I)–(III), no two of ethyl (E)-4-[2-(4-meth­oxy­phen­yl)ethen­yl]-2-methyl­quino­line-3-carboxyl­ate, C22H21NO3, (IV), ethyl (E)-4-[2-(4-bromo­phen­yl)ethen­yl]-2-methyl­quino­line-3-carboxyl­ate, C21H18BrNO2, (V), and ethyl (E)-2-methyl-4-{2-[4-(tri­fluoro­meth­yl)phen­yl]ethen­yl}quino­line-3-carboxyl­ate, C22H18F3NO2, (VI), are isomorphous. The mol­ecules of (IV) are linked by a single C—H...O hydrogen bond to form C(13) chains, but cyclic centrosymmetric dimers are formed in both (V) and (VI). The dimer in (V) contains a C—H...π(pyrid­yl) hydrogen bond, while that in (VI) contains two independent C—H...O hydrogen bonds. Comparisons are made with some related structures, and both the regiochemistry and the mechanism of the heterocyclic ring formation are discussed.",
keywords = "Synthesis, Cyclocondensation, Quinolone, Crystal structure, Molecular conformation, Hydrogen bonding, Supramolecular assembly, Regiochemistry",
author = "Diego Rodr{\'i}guez and Guerrero, {Sergio Andr{\'e}s} and Alirio Palma and Justo Cobo and Christopher Glidewell",
note = "Funding for this research was provided by: Vicerrector{\'i}a de Investigaci{\'o}n y Extensi{\'o}n de la Universidad Industrial de Santander (proyecto No. 2497, to AP); Universidad de Ja{\'e}n, the Consejer{\'i}a de Econom{\'i}a, Innovaci{\'o}n, Ciencia y Empleo (Junta de Andaluc{\'i}a, Spain) and Centro de Instrumentaci{\'o}n Cient{\'i}fico–T{\'e}cnica of the Universidad de Ja{\'e}n (UJA) (to JC).",
year = "2020",
month = sep,
day = "1",
doi = "10.1107/S2053229620010803",
language = "English",
volume = "76",
journal = "Acta Crystallographica Section C Structural Chemistry",
issn = "2053-2296",
publisher = "International Union of Crystallography",
number = "9",

}

RIS (suitable for import to EndNote) - Download

TY - JOUR

T1 - 4-Styrylquinolines from cyclocondensation reactions between (2-aminophenyl)chalcones and 1,3-diketones

T2 - crystal structures and regiochemistry

AU - Rodríguez, Diego

AU - Guerrero, Sergio Andrés

AU - Palma, Alirio

AU - Cobo, Justo

AU - Glidewell, Christopher

N1 - Funding for this research was provided by: Vicerrectoría de Investigación y Extensión de la Universidad Industrial de Santander (proyecto No. 2497, to AP); Universidad de Jaén, the Consejería de Economía, Innovación, Ciencia y Empleo (Junta de Andalucía, Spain) and Centro de Instrumentación Científico–Técnica of the Universidad de Jaén (UJA) (to JC).

PY - 2020/9/1

Y1 - 2020/9/1

N2 - Structures are reported for two matched sets of substituted 4-styryl­quino­lines which were prepared by the formation of the heterocyclic ring in cyclo­condensation reactions between 1-(2-amino­phen­yl)-3-aryl­prop-2-en-1-ones with 1,3-dicarbonyl com­pounds. (E)-3-Acetyl-4-[2-(4-meth­oxy­phen­yl)ethen­yl]-2-methyl­quino­line, C21H19NO2, (I), (E)-3-acetyl-4-[2-(4-bromo­phen­yl)ethen­yl]-2-methyl­quino­line, C20H16BrNO, (II), and (E)-3-acetyl-2-methyl-4-{2-[4-(tri­fluoro­meth­yl)phen­yl]ethen­yl}quino­line, C21H16F3NO, (III), are isomorphous and in each structure the mol­ecules are linked by a single C—H...O hydrogen bond to form C(6) chains. In (I), but not in (II) or (III), this is augmented by a C—H...π(arene) hydrogen bond to form a chain of rings; hence, (I)–(III) are not strictly isostructural. By contrast with (I)–(III), no two of ethyl (E)-4-[2-(4-meth­oxy­phen­yl)ethen­yl]-2-methyl­quino­line-3-carboxyl­ate, C22H21NO3, (IV), ethyl (E)-4-[2-(4-bromo­phen­yl)ethen­yl]-2-methyl­quino­line-3-carboxyl­ate, C21H18BrNO2, (V), and ethyl (E)-2-methyl-4-{2-[4-(tri­fluoro­meth­yl)phen­yl]ethen­yl}quino­line-3-carboxyl­ate, C22H18F3NO2, (VI), are isomorphous. The mol­ecules of (IV) are linked by a single C—H...O hydrogen bond to form C(13) chains, but cyclic centrosymmetric dimers are formed in both (V) and (VI). The dimer in (V) contains a C—H...π(pyrid­yl) hydrogen bond, while that in (VI) contains two independent C—H...O hydrogen bonds. Comparisons are made with some related structures, and both the regiochemistry and the mechanism of the heterocyclic ring formation are discussed.

AB - Structures are reported for two matched sets of substituted 4-styryl­quino­lines which were prepared by the formation of the heterocyclic ring in cyclo­condensation reactions between 1-(2-amino­phen­yl)-3-aryl­prop-2-en-1-ones with 1,3-dicarbonyl com­pounds. (E)-3-Acetyl-4-[2-(4-meth­oxy­phen­yl)ethen­yl]-2-methyl­quino­line, C21H19NO2, (I), (E)-3-acetyl-4-[2-(4-bromo­phen­yl)ethen­yl]-2-methyl­quino­line, C20H16BrNO, (II), and (E)-3-acetyl-2-methyl-4-{2-[4-(tri­fluoro­meth­yl)phen­yl]ethen­yl}quino­line, C21H16F3NO, (III), are isomorphous and in each structure the mol­ecules are linked by a single C—H...O hydrogen bond to form C(6) chains. In (I), but not in (II) or (III), this is augmented by a C—H...π(arene) hydrogen bond to form a chain of rings; hence, (I)–(III) are not strictly isostructural. By contrast with (I)–(III), no two of ethyl (E)-4-[2-(4-meth­oxy­phen­yl)ethen­yl]-2-methyl­quino­line-3-carboxyl­ate, C22H21NO3, (IV), ethyl (E)-4-[2-(4-bromo­phen­yl)ethen­yl]-2-methyl­quino­line-3-carboxyl­ate, C21H18BrNO2, (V), and ethyl (E)-2-methyl-4-{2-[4-(tri­fluoro­meth­yl)phen­yl]ethen­yl}quino­line-3-carboxyl­ate, C22H18F3NO2, (VI), are isomorphous. The mol­ecules of (IV) are linked by a single C—H...O hydrogen bond to form C(13) chains, but cyclic centrosymmetric dimers are formed in both (V) and (VI). The dimer in (V) contains a C—H...π(pyrid­yl) hydrogen bond, while that in (VI) contains two independent C—H...O hydrogen bonds. Comparisons are made with some related structures, and both the regiochemistry and the mechanism of the heterocyclic ring formation are discussed.

KW - Synthesis

KW - Cyclocondensation

KW - Quinolone

KW - Crystal structure

KW - Molecular conformation

KW - Hydrogen bonding

KW - Supramolecular assembly

KW - Regiochemistry

U2 - 10.1107/S2053229620010803

DO - 10.1107/S2053229620010803

M3 - Article

VL - 76

JO - Acta Crystallographica Section C Structural Chemistry

JF - Acta Crystallographica Section C Structural Chemistry

SN - 2053-2296

IS - 9

ER -

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