10.1007/s11172-011-0360-z
The research focuses on the synthesis and photophysical properties of 2-hydroxybenzaldehyde (2-phenylquinazolin-4-yl)hydrazones and their ZnII complexes. The purpose of this study was to extend the synthesis of fluorine-containing quinazoline derivatives and to investigate their potential as luminescent materials, given that nitrogen heterocyclic derivatives with a phenolic OH group are known as effective ligands and many complexes based on o-hydroxy azomethines exhibit luminescent properties. The researchers synthesized a series of new quinazoline derivatives and their zinc(II) complexes, examining their structures and luminescent properties. The chemicals used in this process included 2-aminobenzonitrile, salicylaldehyde, 2-hydroxy-5-nitrobenzaldehyde, 4-hydroxysalicylaldehyde, 3,5-dibromosalicylaldehyde, and various substituted hydrazines. The study concluded that the synthesized hydrazones and their ZnII complexes exhibited interesting photophysical properties, with the complexation process leading to a bathochromic shift in the absorption spectra and blue shifts in the emission peaks. The researchers also noted that the complexation considerably lowered the Stokes shift and increased the quantum yield, suggesting that these quinazoline-containing hydrazones are promising ligand systems for the design of complexes with other metals, potentially useful in electroluminescent materials and organic light-emitting diodes (OLEDs).
10.1080/00397919608003827
The research explores a novel synthetic method for producing N-alkyl o-phenylenediamines through a one-pot phase transfer alkylation and hydrolysis process. The study aims to develop a simple and efficient route for synthesizing these compounds, which are important intermediates in the preparation of isoalloxazines (flavins) and have potential applications in various chemical and pharmaceutical fields. The key chemicals used in this research include o-nitrotrifluoroacetanilides as the starting materials, dimethylsulfate, benzyl bromide, and 1-bromopropane as electrophiles, and tetrabutylammonium chloride or benzyltriethylammonium chloride as phase transfer catalysts. The process involves a one-pot reaction where the o-nitrotrifluoroacetanilides undergo alkylation followed by hydrolysis under phase transfer conditions, yielding N-alkyl o-nitroanilines in good to excellent yields. The study concludes that this method is superior to previous methods involving o-nitroacetanilides due to the increased reactivity and ease of preparation of the trifluoroacetanilides. The findings suggest that this one-pot synthesis provides a convenient and operationally simple approach for the preparation of N-alkyl o-phenylenediamines, which can be further reduced to the desired products.