The transformations of fluoroalkyl-containing 2-arylhydrazono-1,3-dicarbonyl compounds with methylamine |
| |
Authors: | EV Shchegol’kov YaV Burgart VI Saloutin |
| |
Institution: | I.Ya. Postovsky Institute of Organic Synthesis, Urals Branch of the Russian Academy of Sciences, 22/20, S. Kovalevskoy/Akademicheskaya Street, GSP-147, 620041 Ekaterinburg, Russia |
| |
Abstract: | Fluoroalkylated 1,2,3-triketone 2-arylhydrazones and 2-arylhydrazono-3-oxo esters react variously with methylamine depending on the structure of the fluorinated substituent. 2-Arylhydrazono-1,3-dicarbonyl compounds having “short” fluoroalkyl substituents condense with methylamine at the carbonyl group attached to the non-fluorinated substituent whereas ones containing a lengthy polyfluoroalkyl substituent undergo haloformic cleavage as a result of the amine addition at the carbonyl group bearing such a substituent. The resulting 2-arylazo-3-(N-methyl)amino-1-polyfluoroket-2-en-1-ones and 1-(N-methyl)amino-2-arylhydrazono-3-fluoroalkyl-3-oxopropanamides have complexing properties, and they can bind to nickel(II) and copper(II) ions. Nickel chelates can be obtained by a three-component condensation of 2-arylhydrazono-1,3-dicarbonyl compounds and methylamine in the presence of nickel(II) cations. |
| |
Keywords: | Fluoroalkylated 1 2 3-triketone 2-arylhydrazones 2-Arylhydrazono-3-oxo esters Methylamine Condensation Haloformic cleavage Complexation Metalchelate |
本文献已被 ScienceDirect 等数据库收录! |
|