57270-89-0

Basic information

• Product Name: 5-{4-nitrobenzylidene}-1,3-dimethyl-2,4,6(1H,3H,5H)-pyrimidinetrione
• Synonyms: 5-{4-nitrobenzylidene}-1,3-dimethyl-2,4,6(1H,3H,5H)-pyrimidinetrione
• CAS NO: 57270-89-0
• Molecular Formula: C₁₃H₁₁N₃O₅
• Molecular Weight: 289.24354
• Mol File: 57270-89-0.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 5-{4-nitrobenzylidene}-1,3-dimethyl-2,4,6(1H,3H,5H)-pyrimidinetrione(CAS DataBase Reference)
• NIST Chemistry Reference: 5-{4-nitrobenzylidene}-1,3-dimethyl-2,4,6(1H,3H,5H)-pyrimidinetrione(57270-89-0)
• EPA Substance Registry System: 5-{4-nitrobenzylidene}-1,3-dimethyl-2,4,6(1H,3H,5H)-pyrimidinetrione(57270-89-0)

Safety Data

• Hazardous Substances Data: 57270-89-0(Hazardous Substances Data)

Upstream product

• 769-42-6 1,3-dimethylbarbituric acid 
• 555-16-8 4-nitrobenzaldehdye 
• 114656-98-3 1,3-dimethyl-5-(4-nitrobenzyl)pyrimidine-2,4,6(1H,3H,5H)-trione 
• 6642-31-5 6-Amino-1,3-dimethylbarbituric acid 
• 57270-84-5 1,3-dimethyl-5-(4-methyl-benzylidene)-pyrimidine-2,4,6-trione 
• 126178-30-1 N-(4-nitrobenzylidene)-1-phenylmethanamine 
• 57270-82-3 5-(4-methoxy-benzylidene)-1,3-dimethyl-pyrimidine-2,4,6-trione 
• 104-87-0 4-methyl-benzaldehyde 
• 122-52-1 triethyl phosphite 

Downstream Products

• 57270-86-7 5-(4-chlorobenzylidene)-1,3-dimethylbarbituric acid 
• 57270-84-5 1,3-dimethyl-5-(4-methyl-benzylidene)-pyrimidine-2,4,6-trione 
• 126178-30-1 N-(4-nitrobenzylidene)-1-phenylmethanamine 
• 1187642-11-0 12‐(4‐nitrophenyl)‐8,12‐dihydro‐8,10‐dimethyl‐9H‐naphtho[1',2':5,6]pyrano[2,3‐d]pyrimidine‐9,11‐(10H)‐dione 
• 110449-14-4 5-hydroxy-5-(4'-nitrobenzyl-α-d1)-1,3-dimethylbarbituric acid 
• 114702-45-3 5-hydroxy-5-(4'-nitrobenzyl)-1,3-dimethylbarbituric acid 
• 6340-89-2 bis-(2-methyl-indol-3-yl)-(4-nitro-phenyl)-methane 
• 934838-37-6 C₂₁H₁₈N₄O₅ 
• 7501-91-9 3-[(1H-indol-3-yl)(4-nitrophenyl)methyl]-1H-indole 

Relevant articles and documents

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.

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.

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.

A domino knoevenagel-phospha-michael reaction: One-pot synthesis of novel organophosphonates in the presence of multi-walled carbon nanotube?CO?NH(CH2)2NH-SO3H as catalyst

We report a one-pot method for the synthesis of various substituted 1,3-dimethyl-2,4,6-trioxohexahydropyrimidin-5-yl phosphonate derivatives via phosphorus-carbon bond formation through domino Knoevenagel–phospha–Michael reaction. Multi-walled carbon nanotube?CO?NH(CH2)2NH-SO3H was used as an acidic heterogeneous catalyst. The catalyst could be used four times without losing its catalytic activity. The structures of the products were determined by FT-IR spectra, 1H-, 13C- and 31P- Nuclear Magnetic Resonance and elemental analysis. Recovery and reusability of catalyst, simplicity, applicability, good reaction time and good yields of products are the benefits of this work.

“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.

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.

Effect of reaction parameters on the synthesis of 5-arylidene barbituric acid derivatives in ball mills

The influence of crucial reaction parameters on Knoevenagel condensation in planetary ball mills was investigated. Rotation frequency (νrot), milling ball diameter (dMB), milling ball filling degree (φMB), and beaker size

SHIKIMATE PATHWAY INHIBITORS AND THE USE THEREOF

The present invention relates to methods of inhibiting shikimate pathway, comprising administering to a subject a pharmaceutically acceptable composition comprising a compound having a formula: or pharmaceutically acceptable salts thereof. The present invention also provides a synergistic antibacterial composition containing compound

Reaction of 6-aminouracils with aldehydes in water as both solvent and reactant under FeCl3·6H2O catalysis: Towards 5-alkyl/arylidenebarbituric acids

5-Alkyl/arylidenebarbituric acids were efficiently synthesized through an FeCl3·6H2O catalyzed domino reaction of 6-aminouracils, water and aldehydes with water serving a dual role as both solvent and reactant, under benign reaction conditions. A study on comparative substrate scope of 6-aminouracil versus barbituric acid showed similar efficacy towards 5-alkyl/arylidenebarbituric acids. The protocol is the first detailed report to prepare regioselectively 5-alkyl/arylidenebarbituric acids starting from 6-aminouracils, which is an alternative and competing strategy to hitherto all known reactions directly employing barbituric acids. the Partner Organisations 2014.

5-Arylidene N,N-dimethylbarbiturates as urease inhibitors

Earlier 5-arylidene N,N-dimethylbarbiturates 1-24 were reported by our group as novel antioxidant, nevertheless, urease inhibitory activity of these compounds has not been investigated at all. In the present study, compounds 1-24 were synthesized by the reaction of N,N-dimethylbarbituric acid with different aromatic aldehydes, and screened for their in vitro urease inhibitory effects. Compound 7, was found to be most active urease inhibitor in the series. Nonetheless, compounds 11, 12, and 19 were also active against urease enzyme.