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

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, H-1 and C-13 NMR spectroscopy, and high-resolution mass spectrometry, and the structures of the three hybrid products have been determined using singlecrystal X-ray diffraction. Ethyl (E)-2-(1H-benzo[d]imidazol-2-yl)-4-(4-chlorostyryl)quinoline-3-carboxylate, C27H20ClN3O2, (IIIa), and ethyl (E)-2-(1Hbenzo[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 center dot center dot center dot O and C-H center dot center dot center dot pi 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.

Automated summary

Three new hybrids of 4-styrylquinoline-benzimidazole have been synthesized and characterized. The structures of these compounds have been determined and comparisons with related compounds have been made.