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Synthesis, and spectroscopic and structural characterization of three new styrylquinoline–benzimidazole hybrids

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Date
01/11/2022
Author
Ardila, Diana M.
Rodriguez, Diego F.
Palma, Alirio
Diaz, Ivan
Cobo, Justo
Glidewell, Christopher
Keywords
Synthesis
Oxidative cyclocondensation
Styrylquinoline
Benzimidazole
Molecular hybrids
Molecular structure
Molecular conformation
Hydrogen bonding
Supramolecular assembly
Crystal structure
QD Chemistry
DAS
NIS
MCC
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Abstract
Three new 4-styryl­quinoline–benzimidazole hybrids have been synthesized using a reaction sequence in which 2-methyl­quinoline precursors first undergo selective oxidation by selenium dioxide to form the corresponding 2-formyl­quinoline inter­mediates, followed by oxidative cyclo­condensation reactions with benzene-1,2-diamine to yield the hybrid products. The formyl inter­mediates and the hybrid products have all been fully characterized using a combination of IR, 1H and 13C NMR spectroscopy, and high-resolution mass spectrometry, and the structures of the three hybrid products have been determined using single-crystal X-ray diffraction. Ethyl (E)-2-(1H-benzo[d]imidazol-2-yl)-4-(4-chloro­styr­yl)quinoline-3-carboxyl­ate, C27H20ClN3O2, (IIIa), and ethyl (E)-2-(1H-ben­zo[d]imidazol-2-yl)-4-(2-meth­oxy­styr­yl)quinoline-3-carboxyl­ate, C28H23N3O3, (IIIb), both crystallize in the solvent-free form with Z′ = 1, but ethyl (E)-2-(1H-benzo[d]imidazol-2-yl)-4-(4-methyl­styr­yl)quinoline-3-carboxyl­ate, C28H23N3O2, (IIIc), crystallizes as a partial hexane solvate with Z′ = 3, and the ester group in one of the independent mol­ecules is disordered over two sets of atomic sites having occupancies of 0.765 (7) and 0.235 (7). The mol­ecules of (IIIc) enclose continuous channels which are occupied by disordered solvent mol­ecules having partial occupancy. In all of the mol­ecules of (IIIa)–(IIIc), the styryl­quinoline fragment is markedly nonplanar. Different combinations of N—H⋯O and C—H⋯π hydrogen bonds generate supra­molecular assemblies which are two-dimensional in (IIIb) and (IIIc), but three-dimensional in (IIIa). Comparisons are made with the structures of some related com­pounds.
Citation
Ardila , D M , Rodriguez , D F , Palma , A , Diaz , I , Cobo , J & Glidewell , C 2022 , ' Synthesis, and spectroscopic and structural characterization of three new styrylquinoline–benzimidazole hybrids ' , Acta Crystallographica Section C Structural Chemistry , vol. 78 , no. 11 , pp. 671-680 . https://doi.org/10.1107/S2053229622010063
Publication
Acta Crystallographica Section C Structural Chemistry
Status
Peer reviewed
DOI
https://doi.org/10.1107/S2053229622010063
ISSN
2053-2296
Type
Journal article
Rights
Copyright © The Author(s) 2022. 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
Funding for this research was provided by: Vicerrectoría de Investigación y Extensión of the Industrial University of Santander (grant No. 2680)
Collections
  • University of St Andrews Research
URI
http://hdl.handle.net/10023/26246

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