Synthesis, and spectroscopic and structural characterization of three new styrylquinoline–benzimidazole hybrids
Date
01/11/2022Author
Keywords
Metadata
Show full item recordAltmetrics Handle Statistics
Altmetrics DOI Statistics
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
ISSN
2053-2296Type
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
Items in the St Andrews Research Repository are protected by copyright, with all rights reserved, unless otherwise indicated.