Synthesis and solid-state fluorescence of aryl substituted 2-halogenocinchomeronic dinitriles

Abstract

Several novel aryl substituted 2-halogencinchomeronic dinitriles, possessing an intensive solid state fluorescence, were synthesized. The relationship between the chemical structures and photophysical properties of these compounds was investigated.

Design, Sonosynthesis, Quantum‐Chemical Calculations, and Evaluation of New Mono‐ and Bis‐pyridine Dicarbonitriles as Antiproliferative Agents

“…Aliphatic ketones (Table , entries 9—12), however, have less reactivity than aromatic ketones. As compared with the other reported methods, the current protocol is more efficient in terms of time and yield. For instance, it is reported that cyclopentanone ( 2u ) on interaction with TCNE in dioxane at 60—70 o C for 1—2 h, the required product 4u was obtained in 80% .…”

“…Ultrasound will, therefore, be used as a sustainable source of energy during the next experiments to promote the model reaction in polar protic solvents. At increased temperature (60 o C, Table , Entry 13), we detected the isolation of pyrid‐2‐one derivative 7 (Scheme ) as a minor product (a by‐product that was not observed at lower temperatures) that could be attributed to the competitive addition of water (from aqueous HCl) to intermediary ketenimine 5 (Scheme ) …”

“…To overcome this problem, other sources for the generation of HCl in situ , such as acetyl chloride/MeOH, acetyl chloride/ 2‐propanol, oxaloyl chloride/MeOH, and oxaloyl chloride/ 2‐propanol were evaluated at room temperature (Table , entries 14—17). Of them, oxaloyl chloride/MeOH afforded the desired product ( 4a ) in excellent yield (92%) within 25 min at room temperature (Table , entry 16).…”

“…Pyridines are among the most important biochemical scaffolds with broader uses in the medicinal and pharmaceutical industries as well as intermediates in heterocyclic preparations . Among pyridine derivatives, dicyanopyridines act as ‘privileged skeleton’ owing to their prospective uses for therapy . These derivatives were recorded to serve as anti‐prion, human adenosine A2B receptor, antibacterial, anti‐cancer, and anti‐hepatitis B virus .…”

“…In recent years, owing to their broad‐ranging applications, the research on pyridine dicarbonitriles synthesis has attracted particular attention for organic chemists . A variety of 2‐chloropyridine‐3,4‐dicarbonitrile derivatives is accessible and could be prepared from 4‐oxoalkane‐1,1,2,2‐tetracarbonitriles in the existence of aqueous HCl or in dry HCl (acetyl chloride/ propan‐2‐ol) . Comparable protocols for the assembly of 2‐chloropyridine‐3,4‐dicarbonitriles have also been reported via a one‐pot three‐component reaction of tetracyanoethylene (TCNE) and HCl with several ketones .…”