1753-47-5Relevant academic research and scientific papers
Succinimidinium hydrogensulfate ([H-Suc]HSO4) as an efficient ionic liquid catalyst for the synthesis of 5-arylidenepyrimidine-2,4,6(1H,3H,5H)-trione and pyrano-pyrimidinones derivatives
Goli-Jolodar, Omid,Shirini, Farhad,Seddighi, Mohadeseh
, p. 457 - 463 (2016)
In this work, succinimidinium hydrogensulfate ([H-Suc]HSO4), a newly reported Br?nsted acidic ionic liquids is used as an efficient, homogeneous and reusable catalyst for the synthesis of 5-arylidenepyrimidine-2,4,6(1H,3H,5H)-trione and pyrano[2,3-d]-pyrimidine dione derivatives. The products were formed in excellent yields over short reaction times and the catalyst can be reused several times without any appreciable loss in its activity.
1-n-butyl-3-methylimmidazolium tetrafluoroborate-promoted green synthesis of 5-arylidene barbituric acids and thiobarbituric acid derivatives
Wang, Chun,Ma, Jing-Jun,Zhou, Xin,Zang, Xiao-Huan,Wang, Zhi,Gao, Yong-Jun,Cui, Peng-Lei
, p. 2759 - 2764 (2005)
The room temperature ionic liquid 1-n-butyl-3-methylimmidazolium tetra-fluoroborate ([bmim]BF4) was used to promote the synthesis of 5-arylidene barbituric acids and thiobarbituric acid derivatives under the solid-state conditions of grinding or microwave irradiation without organic solvent. The yields were 77.9-96.2%. It is shown that the proposed method is fast, efficient, and environmentally benign. Copyright Taylor & Francis, Inc.
A simple method for knoevenagel condensation of α,β-conjugated and aromatic aldehydes with barbituric acid
Jursic
, p. 655 - 657 (2001)
Several aromatic and α,β-conjugated aromatic aldehydes were condensed with barbituric acid in methanol solution in the absence of acid or base as a catalyst, affording 5-ylidenebarbituric acid derivatives in almost quantitative yields.
CoFe2O4 nanoparticles: An efficient heterogeneous magnetically separable catalyst for "click" synthesis of arylidene barbituric acid derivatives at room temperature
Rajput, Jaspreet Kaur,Kaur, Gagandeep
, p. 1697 - 1704 (2013)
A coprecipitation method was used to synthesize superparamagnetic CoFe 2O4 nanoparticles without using any capping agents/surfactants. The prepared nanoparticles were characterized using Fourier transform infrared spectroscopy, scanning electron microscopy, transmission electron microscopy, X-ray diffraction, a vibrating sample magnetometer (VSM), N2 adsorption and thermogravimetric/differential thermal analysis/differential thermal gravimetry techniques. The synthesized spinel CoFe2O4 nanoparticles had an average size of 2-8 nm with a high surface area (140.9 m2/g). The field-dependent magnetization, demonstrated by VSM and saturation magnetization, was found to be 1.77 emu/g. An efficient method was used for the synthesis of arylidene barbituric acid derivatives using CoFe2O4 magnetic nanoparticles as a magnetically separable and reusable catalyst in aqueous ethanol. The attractive features of this synthetic protocol were very short reaction time, high yields, high turnover frequency, simple work-up procedure, economy, a clean reaction methodology, and chemoselectivity, as well as provision of an ecofriendly and green synthesis.
Preparation of benzylidene barbituric acids promoted by infrared irradiation in absence of solvent
Alcerreca, Guadalupe,Sanabria, Ruben,Miranda, Rene,Arroyo, Gabriel,Tamariz, Joaquin,Delgado, Francisco
, p. 1295 - 1301 (2000)
Several benzaldehydes were condensed with barbituric acid under infrared irradiation, in absence of solvent, affording the corresponding 5-benzylidene barbituric acids.
Organic reactions in ionic liquids: Ionic liquid promoted Knoevenagel condensation of aromatic aldehydes with (2-thio)barbituric acid
Hu, Yi,Chen, Zhen-Chu,Le, Zhang-Gao,Zheng, Qin-Guo
, p. 4521 - 4529 (2004)
The Knoevenagel condensation of aromatic aldehydes with (2-thio)barbituric acid proceeded efficiently in reusable ionic liquids, EAN, BmimBF4, and BmimPF6 at room temperature in the absence of any catalyst with high yields.
Synthesis and Antimycobacterial Activity of 5-(Arylmethylene)Hexahydropyrimidine-2,4,6-Triones
Luzhnova,Tyrkov,Gabitova
, p. 810 - 812 (2016)
A series of 5-(arylmethylene)hexahydropyrimidine-2,4,6-triones were synthesized. Their antimycobacterial activity and acute daily toxicity with respect to M. lufu were investigated.
The synthesis and evaluation of near-infrared probes with barbituric acid acceptors for in vivo detection of amyloid plaques
Zhou, Kaixiang,Fu, Hualong,Feng, Liang,Cui, Mengchao,Dai, Jiapei,Liu, Boli
, p. 11665 - 11668 (2015)
A new array of near-infrared probes containing barbituric acid acceptors has been developed as Aβ imaging agents. These probes displayed long-emission wavelengths and large Stokes shifts, as well as high affinities for Aβ aggregates. In vivo and ex vivo studies demonstrated that BBTOM-3 could intensely label Aβ plaques in the brains of transgenic mice.
SiO2?12WO3?24H2O: A highly efficient catalyst for the synthesis of 5-arylidene barbituric acid in the presence of water
Li, Ji-Tai,Sun, Ming-Xuan
, p. 353 - 355 (2009)
The condensation of aromatic aldehydes and barbituric acid catalyzed by SiO212WO324H2O in aqueous media at room temperature gave 5-arylidene barbituric acid in high yields with or without the use of ultrasound, providing a simple and efficient route to synthesis of these compounds.
Assessing the potential of para-donor and para-acceptor substituted 5-benzylidenebarbituric acid derivatives as push–pull electronic systems: Experimental and quantum chemical study
Stojiljkovi?, Ivana N.,Ran?i?, Milica P.,Marinkovi?, Aleksandar D.,Cvijeti?, Ilija N.,Mil?i?, Milo? K.
, (2021)
Electronic interactions in donor-π-linker-acceptor systems with barbituric acid as an electron acceptor and possible electron donor were investigated to screen promising candidates with a push–pull character based on experimental and quantum chemical studies. The tautomeric properties of 5-benzylidenebarbituric acid derivatives were studied with NMR spectra, spectrophotometric determination of the pKa values, and quantum chemical calculations. Linear solvation energy relationships (LSER) and linear free energy relationships (LFER) were applied to the spectral data - UV frequencies and 13C NMR chemical shifts. The experimental studies of the nature of the ground and excited state of investigated compounds were successfully interpreted using a computational chemistry approach including ab initio MP2 geometry optimization and time-dependent DFT calculations of excited states. Quantification of the push–pull character of barbituric acid derivatives was performed by the 13CNMR chemical shift differences, Mayer π bond order analysis, hole-electron distribution analysis, and calculations of intramolecular charge transfer (ICT) indices. The results obtained show, that when coupled with a strong electron-donor, barbituric acid can act as the electron-acceptor in push–pull systems, and when coupled with a strong electron-acceptor, barbituric acid can act as the weak electron-donor.
