57270-82-3

Usage

InChI:InChI=1/C14H14N2O4/c1-15-12(17)11(13(18)16(2)14(15)19)8-9-4-6-10(20-3)7-5-9/h4-8H,1-3H3

Upstream product

• 769-42-6 1,3-dimethylbarbituric acid 
• 123-11-5 4-methoxy-benzaldehyde 
• 6642-31-5 6-Amino-1,3-dimethylbarbituric acid 
• 114656-99-4 5-(4-methoxybenzyl)-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione 
• 622-72-0 N-(4-methoxylbenzylidene)benzylamine 
• 57270-84-5 1,3-dimethyl-5-(4-methyl-benzylidene)-pyrimidine-2,4,6-trione 
• 57270-86-7 5-(4-chlorobenzylidene)-1,3-dimethylbarbituric acid 
• 54459-73-3 5-benzylidene-1,3-dimethyl-pyrimidine-2,4,6-trione 
• 836-41-9 p-methoxybenzylidene-phenylamine 
• 34946-82-2 copper(I) triflate 

Downstream Products

• 143208-52-0 5-(4-Methoxy-phenyl)-1,3-dimethyl-6-phenylamino-1H-furo[2,3-d]pyrimidine-2,4-dione 
• 114656-99-4 5-(4-methoxybenzyl)-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione 
• 209798-64-1 7,7-bis(dimethylamino)-6,6-difluoro-1,3-dimethyl-5-(4'-methoxyphenyl)-1,3,4,5,6,7-hexahydro-2H-pyrano[2,3-d]pyrimidine-2,4-dione 
• 959833-62-6 1,3-dimethyl-5-[1-(4-methoxyphenyl)-3-oxo-3-phenylpropyl]pyrimidine-2,4,6(1H,3H,5H)-trione 

Relevant academic research and scientific papers

Metal Ion-Driven Constitutional Adaptation in Dynamic Covalent C=C/C=N Organo-Metathesis

Knoevenagel barbiturate derivatives and imines are able to undergo efficient component recombination through dynamic covalent C=C/C=N organo-metathesis in absence of a catalyst. A [2×2] dynamic covalent library (DCL) containing two Knoevenagel derivatives Kn1 and Kn2 and two imines A1 and A2 has been established and its adaptive features in response to the addition of metal cations have been investigated. Addition of Cu(I) triflate as an effector, induces fast and remarkable constitutional selection of the DCL towards amplification of the Cu(I)-A2 complex and its agonist Kn1. This adaptation process could be reversed by addition of neocuproine as a competitive Cu(I) ligand. Furthermore, separate addition of five other metal cations as input agents, i. e. Ag(I), Fe(II), Zn(II), Cu(II) and Li(I), led to the generation of cation-specific distribution patterns as outputs, showing the ability of the present DCL to recognize different effectors.

L-Proline based ionic liquid: A highly efficient and homogenous catalyst for synthesis of 5-benzylidene-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione and pyrano[2,3-d] pyrimidine diones under ultrasonic irradiation

A catalytic, practical, efficient procedure for the synthesis of 5-benzylidene-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione and pyrano[2,3-d] pyrimidine diones at room temperature was developed using L-Proline nitrate ionic liquid under ultrasonic irradiation. The L-Proline nitrate is homogeneous and green catalyst easy to prepare by mixing L-Proline and nitric acid possess excellent catalytic activity under standard ultrasonic bath at room temperature for the synthesis of pyrimidine core. This adequate procedure offers some advantages like the use of green solvent H2O, environmentally green benign procedure, excellent yields, simple procedure, short reaction times, no need for column chromatographic separation and reusability of catalyst for five subsequent reaction.

One-Pot Knoevenagel and [4 + 2] Cycloaddition as a Platform for Calliviminones

Bioactive compounds featuring an unusual core of spiro[5.5]undecenes and calliviminones were synthesized in very good yield with good regio- and diastereoselectivities through a one-pot Knoevenagel and [4 + 2] cycloaddition from the readily available aldehydes, cyclic-1,3-diones, dienes, and a catalytic amount of (s)-proline.

Palladium-Catalyzed [5 + 2] Annulation of Vinylethylene Carbonates with Barbiturate-Derived Alkenes

A palladium/XantPhos-catalyzed [5 + 2] annulation of VECs with electron-deficient alkenes having an isolated carbon-carbon double bond has been developed to afford spirobarbiturate-tetrahydrooxepines. This study provides an expedient assembly of biologically interesting spirobarbiturate-tetrahydrooxepines. The easy scalability and versatile transformability of the reaction products were also exhibited.

Synthesis of spirobarbiturate-pyrrolidinones: Via a domino aza-Michael/SN2 cyclization of barbiturate-derived alkenes with N-alkoxy α-haloamides

A highly efficient domino aza-MIRC (Michael Induced Ring Closure) reaction between barbiturate-derived alkenes and N-alkoxy α-haloamides has been achieved in moderate to excellent yields. This reaction proceeds smoothly under mild conditions via a domino aza-Michael addition/intramolecular SN2 sequence, providing a practical tool in the synthesis of bioactive molecules spirobarbiturate-3-pyrrolidinones.

Tosylmethylisocyanide (TosMIC) [3+2] cycloaddition reactions: A facile Van Leusen protocol for the synthesis of the new class of spirooxazolines, spiropyrrolines and Chromeno[3,4-c]pyrrols

The reactivity and chemo-, regio- and diastreo-selectivity of tosylmethyl isocyanides (TosMIC) are investigated in Van Leusen type [3 + 2] cycloaddition reactions with the various activate cyclic ketones and double C–C bonds in the synthesis of spirooxazolines, spiropyrrolines and chromeno[3,4-c]pyrrols in good to excellent yields under catalyst-free conditions without any activation at ambient temperature.

Dynamic Covalent Metathesis in the C=C/C=N Exchange between Knoevenagel Compounds and Imines

Fast and reversible dynamic covalent C=C/C=N exchange takes place without catalyst in nonpolar solvents between barbiturate-derived Knoevenagel (Kn) compounds and imines. A detailed study of the reaction indicates that it proceeds by an associative organo-metathesis mechanism involving the formation of a four-membered ring azetidine intermediate by addition of the imine C=N group to the C=C bond of the Kn compound. This intermediate could be generated cleanly and stabilized at low temperature by condensation of the o,p-dinitrophenyl Kn derivative with the cyclic imine 1-azacyclohexene. It was characterized by extensive NMR and mass spectrometric studies. The process described represents a genuine dynamic covalent organo-metathesis through a four-membered ring adduct as intermediate. It paves the way for the exploration of a wide set of dynamic systems involving (strongly) polarized C=C bonds and various imines, extending also into covalent dynamic polymers and polymolecular assemblies.

Efficient one-pot synthesis of some new pyrimido[5′,4′:5,6]pyrido[2,3-d]pyrimidines catalyzed by magnetically recyclable Fe3O4 nanoparticles

The study is devoted to one-pot reaction of 1,3-dimethylbarbituric acid with aromatic aldehydes and ammonium acetate using Fe3O4 nanoparticles as efficient and magnetically recyclable catalysts. Aromatic aldehydes substituted with electron-withdrawing groups or none, reacted successfully with 1,3-dimethylbarbituric acid and ammonium acetate to give new pyrimido[5′,4′:5,6]pyrido[2,3-d]pyrimidine derivatives (can be also named as pyrido[2,3-d:6,5-d′]dipyrimidines) in high yields over relatively short reaction time. The Knoevenagel condensation products were isolated using aromatic aldehydes bearing electron-donating substituents. The catalyst could be efficiently used for four times without substantial reduction in its activity. The new products were characterized on the basis of FT-IR, 1H NMR and 13C NMR spectral data.

Diversity-oriented Multicomponent Heterocyclizations Involving Derivatives of 3(5)-Aminoisoxazole, Aldehydes and Meldrum's or N,N′-Dimethylbarbituric Acid

5-Amino-3-methylisoxazole and 3-amino-5-methylisoxazole were studied in details in the multicomponent heterocyclizations with aromatic aldehydes and Meldrum's or N,N′-dimethylbarbituric acid with help of classical and non-classical (microwave and ultrasonic irradiation) activation methods.

“On-water” catalyst-free, one-pot synthesis of quaternary centered and spiro-tetrahydrothiophene-barbiturate hybrids

A green and efficient method have been developed for the synthesis of quaternary centered and spiro-barbiturate-tetrahydrothiophene hybrids via Knoevenagel condensation,1,4-thia-Michael and intramolecular Aldol reactions using “on water” concept under catalyst-free conditions. Systematic studies were carried out to find the role of the water and total reaction concentration (0.086?M) to promote the reaction in two steps (one-pot). The use of water as a reaction medium, catalyst-free conditions, broad substrate scope, one-pot approach for the creation of quaternary centered and spiro molecules are the advantages of this method.