6340-72-3Relevant academic research and scientific papers
An eco-friendly and highly efficient synthesis of pyrimidinones using a TiO2-CNTs nanocomposite catalyst
Khalilian, Shahin,Abdolmohammadi, Shahrzad,Nematolahi, Fereshteh
, p. 361 - 367 (2017/07/24)
Background: The recent development of using heterogeneous catalysts in organic synthesis has increased the need for fine metal oxide nanoparticles. Nanosized titanium dioxide nanoparticles (TiO2 NPs) can be used in several organic and inorganic transformations because of their superior properties such as high catalytic activity, non-toxicity, easily availability, moisture stability and reusability. Pyrimidinones are privileged heterocycles in the field of drugs and pharmaceutical industry. Method: The current methodology deals with the direct assembly of Meldrum’s acid, aromatic aldehydes, and guanidine nitrate in the presence of a catalytic amount of the synthesized TiO2-CNTs nanocomposite could be utilized to afford 2-amino-6-aryl-5,6-dihydro-4(3H)-pyrimidinones under solventfree conditions within 2-3 h. Results: A series of 2-amino-6-aryl-5,6-dihydro-4(3H)-pyrimidinones were synthesized in high yields (90-98%) via a simple one-pot three-component coupling reaction using the synthesized TiO2-CNTs nanocomposite with the weight ratio of 50:50 as an efficient and recyclable catalyst. All synthesized compounds were well characterized by their satisfactory elemental analyses, IR, 1H and 13C NMR spectroscopy. The synthesized catalyst was fully characterized by XRD, SEM, and elemental analysis. Conclusion: We have developed a general and highly efficient TiO2-CNTs nanocomposite catalyzed procedure for the synthesis of 2-amino-6-aryl-5,6-dihydro-4(3H)-pyrimidinones from a one-pot three-component coupling reaction of Meldrum’s acid, aromatic aldehydes, and guanidine nitrate with high yields under solvent-free conditions. This new protocol has revealed several advantages such as recyclability of catalyst, short reaction times, high to excellent yields of products and solvent-free conditions.
Reaction of polyfluorinated chalcones with guanidine
Borodina,Orlova,Gatilov,Sal'Nikova
, p. 1745 - 1752 (2016/02/03)
Reactions of polyfluorinated chalcones with guanidine in the presence of bases are accompanied by elimination of the polyfluorophenyl group. 3-(Pentafluorophenyl)-1-phenylprop-2-en-1-one and its derivatives reacted with guanidine under basic conditions to give 4-phenylpyrimidin-2-amine, polyfluorobenzenes, and Michael adducts, 3-(2-amino-4-phenylpyrimidin-5-yl)-3-(4-R-2,3,5,6-tetrafluorophenyl)-1-phenylpropan-1-ones. 1-(Pentafluorophenyl)-3-phenylprop-2-en-1-one and 1,3-bis(pentafluorophenyl)prop-2-en-1-one were converted into cinnamic acid derivatives whose reaction with guanidine afforded 2-amino-6-aryl-5,6-dihydropyrimidin-4(1H)-ones.
Amino-functionalized MCM-41 base-catalyzed one-pot synthesis of 2-amino-5,6-dihydropyrimidin-4(3H)-ones
Mirza-Aghayana,Lashakia, T. Baie,Rahimifarda,Boukherroubb,Tarlania
experimental part, p. 280 - 286 (2011/12/21)
A simple and efficient one-pot method for the preparation of 2-amino-5,6-dihydropyrimidin-4(3H)-one from the cyclocondensation of Meldrum's acid, aldehydes and guanidinium carbonate using a catalytic amount of amino-functionalized MCM-41 is described. Thi
Efficient synthesis of 2-amino-6-aryl-5,6-dihydro -3#-pyrimidin-4-one building blocks via domino reaction
Mohammadnejad, Mahdieh,Hashtroudi, Mehri S.,Balalaie, Saeed
experimental part, p. 459 - 465 (2010/09/20)
One-pot three component condensation of Meldrum's acid, benzaldehyde derivatives and guanidinium carbonate leads to 2-amino-6-aryl-5,6-dihydro-3H- pyrimidin-4-one derivatives in good yields. The products can be utilized in the synthesis of diverse heterocyclic compounds libraries.
Application of fragment-based lead generation to the discovery of novel, cyclic amidine β-secretase inhibitors with nanomolar potency, cellular activity, and high ligand efficiency
Edwards, Philip D.,Albert, Jeffrey S.,Sylvester, Mark,Aharony, David,Andisik, Donald,Callaghan, Owen,Campbell, James B.,Carr, Robin A.,Chessari, Gianni,Congreve, Miles,Frederickson, Martyn,Folmer, Rutger H. A.,Geschwindner, Stefan,Koether, Gerard,Kolmodin, Karin,Krumrine, Jennifer,Mauger, Russell C.,Murray, Christopher W.,Olsson, Lise-Lotte,Patel, Sahil,Spear, Nate,Tian, Gaochao
, p. 5912 - 5925 (2008/04/12)
Fragment-based lead generation has led to the discovery of a novel series of cyclic amidine-based inhibitors of β-secretase (BACE-1). Initial fragment hits with an isocytosine core having millimolar potency were identified via NMR affinity screening. Stru
