Fluoroalkyl-containing 2-arylhydrazono-1,3-dicarbonyl compounds in the reactions with ethylenediamine and polyethylenepolyamines

The interaction of fluorinated 2-arylhydrazono-1,3-dicarbonyl compounds with o-phenylenediamine

“…So, the formation of N,N 0 -ethylenebis(2-arylazo-1,3-aminovinylketones) and N,N 0 -ethylenediamides from 2-arylhydrazono-1,3-dicarbonyl compounds and ethylenediamine (pKa 1 ¼ 10.09, pKa 2 ¼ 7.00 [13]) occurs at room temperature [6], while the reactions of 2-arylhydrazono-1,3-dicarbonyl compounds with o-phenylenediamine having lower basicity (pKa 1 ¼ 4.47, pKa 2 < 2 [13]) proceed only upon heating in o-xylene or toluene. However the using a template method in the reactions of 1,2,3-triketone 2-arylhydrazones with o-phenylenediamine results in the acyclic products formation like the reactions of these compounds with ethylenediamine.…”

“…Earlier it has been shown that nickel(II) complexes can be obtained by one-step template method from ethylenediamine and 1,2,3-triketone 2-arylhydrazones 2 in the presence of nickel(II) acetate [6]. We have found that 1,2,3-triketone 2-arylhydrazones 2a,d,f undergo template condensation with o-phenylenediamine to form nickel(II) N,N 0 -phenylene-bis(2-arylazo-1,3-aminovinylketones) 11a-c (Scheme 6).…”

“…Previously we obtained fluoroalkyl-containing 2-arylhydrazono-1,3-dicarbonyl compounds and studied their reactions with a-N,N-, N,O-dinucleophiles [5], ethylenediamine and polyethylenepolyamines [6]. In this paper the interaction of fluorine-containing 2-arylhydrazono-3-oxo esters 1 and 1,2,3-triketone 2-arylhydrazones 2 with o-phenylenediamine are described.…”

Microwave-assisted synthesis of fused heterocycles incorporating trifluoromethyl moiety

“…Recently, new methodologies of fluorination have been shown to be more elegant and applicable than conventional fluorination methods such as electrochemical fluorination [20][21][22][23][24] or using various fluorine-containing building blocks [25][26][27]. In this context, trifluoromethylated 1,3-dicarbonyl derivatives constitute important synthetic intermediates, incorporating multiple functionalities that can be involved either as nucleophilic or electrophilic species in a large variety of synthetic transformations [28][29][30][31]. Their versatility and effectiveness as potential multicomponent substrates have been proven to be building blocks for a wide variety of trifluoromethyl-substituted heterocyles.…”