New photochromic derivatives of 2-styrylquinoline and 2-styrylquinoxaline were obtained by the condensation of the methyl derivatives of the mentioned heterocycles with substituted benzaldehydes in the presence of basic and acidic catalysts, and also under the conditions of Wittig reaction. The structure of compounds obtained was proved by physicochemical analysis methods including XRD.Styryl-substituted derivatives of quinoline and quinoxaline are interesting as compounds with a potential biological activity. The derivatives of quinoline and quinoxaline possess bactericidal and fungicidal properties [1,2]. It was shown recently that quinoline derivatives are promising substrates for the photoinduced electrocyclic reaction [3]. The synthetic potential of these phototransformations is suffi ciently wide and makes it possible to use them for the synthesis of new polyfused heteroaromatic compounds (Scheme 1).π-Conjugated organic compounds based on aromatic systems attract signifi cant attention with respect to the application as semiconductors in organic fi eld transistors (OFETs), organic light-emitting diodes (OLEDs), and photogalvanic batteries, and also as biological active compounds, e.g., potential antitumor agents [4].It is known [5][6][7][8][9][10][11][12] that the main procedure for the synthesis of styrylheterocycles is the aldol-type condensation of methyl derivatives of heterocyclic bases with benzaldehyde derivatives. The primary conditions of the condensation contained the use of relatively strong protic acids and bases, and the range of the possible reaction products was limited. Yet the importance of this condensation as one of the main procedures for the preparation of the polyfunctional products is so high that the development of various versions of its performance becomes nowadays a special fi eld of research.We tested this method for the synthesis of methoxysubstituted 2-styrylquinoline (II). The acidity characteristic of the alkyl groups in the α-position of the pyridine Scheme 1. N X R 2 R 1 hv N X R 2 R 1 and/or N X R 2 R 1 X = CH, N.
The crystal and molecular structures of 2 styrylquinoxaline derivatives with different substituents in the styryl fragment are determined. The degree of planarity of the molecules studied varies in a very wide range, from 1.7° to 33.5°. In the ethylene fragment, the double bond is essentially localized. The bicycle pedal disordering of the ethylene fragment is found in the crystals of the methoxy and oxyacetyl derivatives of 2 styrylquinoxaline. None of the packings contains packing motifs favorable for the photocycloaddition (PCA) reaction with single crystal retention. The crystal packings of these compounds and that of 2 (4 meth ylstyryl)quinoxaline are characterized by a stacking motif of the head to head type, which eliminates the possibility of PCA taking place with single crystal retention but is suitable for this reaction in polycrystalline films. The crystal packing of 2 (3,4 dimethoxystyryl)quinoxaline does not contain elements with stacking interactions.
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