Condensation of methyl substituted six membered heteroaromatics containing one or two nitrogen atoms with aldehyde derived from benzo 15 crown 5 ether in DMF in the presence of Bu t OK afforded 15 crown 5 containing hetarylphenylethenes. According to the results of NMR spectroscopy, these compounds exist as mixtures of syn and anti conformers in solution (MeCN d 3 ). The structures of two compounds were established by X ray diffraction analysis.Ligands based on substituted pyridines, in which the cyclic nitrogen atom can form strong coordination bonds with metal cations and hydrogen bonds with carboxy and ammonium groups of other organic molecules, 1 are widely used for designing supramolecular assemblies. 2 It is ex pected that such ligands and supramolecular assemblies based on these ligands can be used for molecular recogni tion of chiral molecules 3,4 and the design of molecular devices having good luminescence characteristics 5,6 and materials for optoelectronics 7,8 and find application in electrochemical analysis as well. 9Hetarylphenylethenes based on pyridine, quinoline, dipyridyl, 3H indole, benzothiazole, and benzoxazole can be prepared by condensation of methyl substituted het erocyclic bases with substituted benzaldehydes under ba sic (Py, 10,11 piperidine, 12 Bu t OK, 13 AlkONa (Alk = Me or Et), 14,15 or LDA 16 ) or acidic (ZnCl 2 , 17,18 HCl, 19 ace tic acid, or acetic anhydride 20,21 ) conditions. The synthe sis of hetarylphenylethenes by the Wittig reaction was also documented. 22 The synthesis and properties of heterocyclic analogs of stilbene containing a macrocyclic fragment were con sidered in several publications. 23-29 It was noted that this class of compounds holds promise for the design of opti cal sensors for metal cations. 30 In the present study, we used six membered hetero aromatic bases containing one or two nitrogen atoms in the ring (Scheme 1) as the heterocyclic component and analyzed the influence of the structure of the heterocyclic component on the formation of the corresponding crown containing hetarylphenylethenes.
Scheme 1Reagents and conditions: AlkOM = MeONa or Bu t OK; DMSO or DMF as the solvent.Condensation of azine derivatives 1a-g with 4´-formylbenzo 15 crown 5 ether (2a) or 3,4 dimethoxy benzaldehyde (2b) was carried out at room temperature