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
• Article Data: 27

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

Downstream Products

• 143208-53-1 1,3-Dimethyl-5-(4-nitro-phenyl)-6-phenylamino-1H-furo[2,3-d]pyrimidine-2,4-dione 
• 114657-02-2 1,3-dimethyl-5-(4'-nitrophenyl)phenylthiomethylbarbituric acid 
• 155859-64-6 5-[Benzylsulfanyl-(4-nitro-phenyl)-methyl]-1,3-dimethyl-pyrimidine-2,4,6-trione 
• 114656-98-3 1,3-dimethyl-5-(4-nitrobenzyl)pyrimidine-2,4,6(1H,3H,5H)-trione 
• 110449-13-3 5-(4'-nitrobenzyl-α-d1)-1,3-dimethylbarbituric acid 
• 934838-37-6 C₂₁H₁₈N₄O₅ 
• 7501-91-9 3-[(1H-indol-3-yl)(4-nitrophenyl)methyl]-1H-indole 
• 6340-89-2 bis-(2-methyl-indol-3-yl)-(4-nitro-phenyl)-methane 
• 114702-45-3 5-hydroxy-5-(4'-nitrobenzyl)-1,3-dimethylbarbituric acid 
• 110449-14-4 5-hydroxy-5-(4'-nitrobenzyl-α-d1)-1,3-dimethylbarbituric acid 
• 118823-33-9 1,3,5-trimethyl-5-(4'-nitrophenyl)phenylthiomethylbarbituric acid 

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.

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.

“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.