80220-75-3Relevant academic research and scientific papers
Hydrazones, ArNHN=CRCH2COX, from reactions of arylhydrazines, ArNHNH2, with 1,3-dicarbonyl compounds, RCOCH2COX(X = OR1 or NHPh): Crystal structures of (E)-4-O2NC 6H4NHN=CMeCH2CO2R1 (R1 = Me or Et) and (E)-PhNHN=CPhCH2CONHPh
De Lima, Geraldo M.,Wardell, James L.,Wardell, Solange M. S. V.
experimental part, p. 213 - 221 (2011/08/02)
The molecular and crystal structures of (E)-4-O2NC 6H4NHN=CMeCH2CO2R1 (4: R1 = Me; 5: R1 = Et) and (E)-PhNHN=CPhCH2CONHPh (6) are reported from data collected at 120(2) K. The major intermolecular interactions in both 4 and 5 involve the hydazonyl NH and the carbonyl oxygen, with formation of symmetric dimers. Due to 4 and 5 each having different sets of additional intermolecular interactions, different supramolecular arrays are produced: molecules of 4 are linked into a three-dimension structure, while zig-zag chains of molecules of 5 are obtained. Chains of molecules of 6, prepared from PhNHNH2 and PhCOCH2CONHPh, are obtained from intermolecular hydrogen bonds involving amido NH and carbonyl oxygen moieties. Further interactions, C-H-π(arene), C-H-O and π-π stacking interactions in 6 produces a three dimensional array. Compound 4 crystallizes in the triclinic space group P - 1 with a = 7.7027(2) A, b = 7.8103(2) A, c = 11.1761(3) A, α = 77.054(2)°, β = 79.425(2)°, γ = 81.097(2)°. Compound 5 crystallizes in the triclinic space group P - 1 with a = 5.6323(2)A, b = 9.9695(3)A, c = 11.0286(4)A, α = 91.859(2)°, β = 102.034(2)°, γ = 98.898(3)°. Compound 6 crystallizes in the monoclinic space group P21/c with a = 10.4255(8)A, b = 10.4255(8)A, c = 9.3368(5)A, β = 113.780(4) °.
Ring Opening and Substitution Reactions of 4,4-Dihalo-pyrazolin-5-ones with Nucleophiles
Kirschke, Klaus,Lutze, Gerhard,Schmitz, Ernst
, p. 367 - 373 (2007/10/02)
1-Aryl-4,4-dihalo-3-methyl-pyrazolin-5-ones (1a-c) undergo ring opening with alkoxides and form alkyl 3-arylazo-2-halo-2-butenoates (2a-d).Analogous reactions take place with ammonia and amines. 4-Nitro-phenoxide reacts with substitution of both halogens to the 4,4-bis(4-nitro-phenyl)-compound (5).Phenols are selectively ortho-brominated by the title compounds 1a and b.
