کد مقاله | کد نشریه | سال انتشار | مقاله انگلیسی | نسخه تمام متن |
---|---|---|---|---|
1314135 | 1499338 | 2014 | 5 صفحه PDF | دانلود رایگان |
• Polyfluorochalcones with 1,2-diaminobenzene give benzo-1H-1,5-diazepine derivatives.
• Polyfluorobenzo-1H-1,5-diazepines transform to tetracyclic benzimidazoquinolines.
• The structures are confirmed by X-ray.
Interaction of polyfluorinated chalcones (pentafluorobenzalacetophenone, benzalpentafluoroacetophenone and decafluorochalcone) with 1,2-diaminobenzene in alcohols in the presence of triethylamine or quaternary ammonium salt (TEBAC) has been investigated. In the presence of TEBAC in 2-propanol polyfluorinated 2,4-diaryl-2,3-dihydro-1H-1,5-benzodiazepines are formed. Some of them undergo intramolecular fluorine substitution and unusual rearrangement into a previously unknown polyfluoro-containing tetracyclic compounds—(6aR)-1,2,3,4-tetrafluoro-6a-aryl-6a,7-dihydrobenzimidazo[1,2-a]quinolines, under the reaction conditions as well as in absence of TEBAC. The structures are established on NMR spectra and confirmed by X-ray.
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Journal: Journal of Fluorine Chemistry - Volume 162, June 2014, Pages 66–70