40640-41-3Relevant academic research and scientific papers
Uses of dimedone for the synthesis of new heterocyclic derivatives with anti-tumor, c-Met, tyrosine, and Pim-1 kinases inhibitions
Mohareb, Rafat M.,Al Farouk, Fatma O.,Wardakhan, Wagnat W.
, p. 1984 - 2003 (2018)
The reaction of dimedone (1) with any of the diazonium salts 2a–c to give the arylhydrazone derivatives 3a–c. The Gewald’s reaction of any of compounds 3a–c using elemental sulfur and either of malononitrile or ethyl cyanoacetate gave the thiophene deriva
Synthesis of arylhydrazone-based molecular switches using aryldiazonium silica sulfate nanocomposites and analysis of their isomerization
Abbaspourrad, Alireza,Aghaei, Hamidreza,Chermahini, Alireza Najafi,Khazdooz, Leila,Soltani, Solmaz,Zarei, Amin
, (2021/06/26)
A fast and efficient method for the synthesis of a series of arylhydrazones by reacting aryldiazonium silica sulfate nanocomposites with malononitrile, ethyl acetoacetate and dimedone is reported. All reactions were carried out in water at room temperature and the corresponding products were obtained in 77–87% yields. The existence of two kinds of intramolecular hydrogen bonds in the arylhydrazones synthesized using ethyl acetoacetate enables these compounds to be switched by rotation about the hydrazone C[dbnd]N bond, which leads to a reversible isomerization between their E and Z configurations. This switching can be controlled by changing the polarity of the solvents. The E/Z ratio of each synthesized compound was studied in CHCl3 and DMSO. The ratios of the E/Z were calculated using 1H NMR data in both CDCl3 and DMSO?d6, and used to calculate ΔG° for the E-Z isomerization of each synthesized compound in these two solvents. By changing the solvent from CHCl3 to DMSO, the E/Z ratios decreased. The results demonstrated that the ΔG° values for the formation of Z isomers were more negative than those of the E isomers in DMSO. This is why Z isomers are more stable than E isomers in DMSO. The results of density functional theory (DFT) calculations at B3LYP/6–311++G (d,p) level of theory, were in agreement with the experiments and confirmed the increased stability of Z isomers in DMSO. In most cases, DFT calculation in CDCl3 and DMSO indicate that the dipole moments of the Z isomers are significantly higher than those of the E isomers. Finally, the effect of temperature on the E-Z isomerization was studied using dynamic 1H NMR. The findings demonstrated that temperature does not have any significant effect on the E-Z isomerization in CDCl3 and DMSO?d6.
A microwave assisted diazo coupling reaction: The synthesis of alkylazines and thienopyridazines
Al-Mousawi, Saleh,Elassar, Abdel-Zaher,El-Apasery, Morsy
, p. 1755 - 1771 (2007/10/03)
Heating diazoaminobenzene with active methylene compounds 1-3 in microwave oven in acetic acid, in the presence of hydrochloric acid, afforded the corresponding arylhydrazones 5-7. These reaction products were condensed with ethyl cyanoacetate in a domestic microwave oven after 1-2 minutes heating to yield the pyridazinones 8-12. Compounds 8c and 12 reacted with sulfur in basic DMF solution, in microwave oven using MORE technology to yield the thienopyridazinone 14 and 16 respectively. While 17 was produced when 8b was treated like wise with sulfur and DMF in the presence of piperidine. Compounds 16 coupled with aromatic diazonium salts to yield arylazo derivatives 21a-c. Copyright Taylor & Francis Group, LLC.
Phenylhydrazone Derivatives of Dimedone: Hydrogen Bonding, Spectral (13C and 1H Nuclear Magnetic Resonance) and Conformational Considerations. Crystal and Molecular Structures of 5,5-Dimethylcyclohexane-1,2,3-trione 2-(4-Methylphenylhydrazone) (1) and 5,5
Drew, Michael G. B.,Vickery, Brian,Willey, Gerald R.
, p. 1297 - 1304 (2007/10/02)
A series of phenylhydrazone derivatives of 5,5-dimethylcyclohexane-1,3-dione (dimedone) have been prepared.Their i.r. and 1H n.m.r. spectra are discussed in terms of the extent of intramolecular hydrogen bonding.With o-nitro-group substituents on the arom
