54459-73-3

Usage

Type of compound

Cyclic α-diketone

Reactant use

Formation of dihydroxy compounds through cyclic dioximes

Physical state

Yellow crystalline solid

Melting point

81-83°C

Solubility

Insoluble in water, soluble in organic solvents (e.g., ethanol, acetone)

Applications

Preparation of heterocycles, pharmaceuticals, and study of chemical reactions and mechanisms

Safety precautions

Causes irritation to skin, eyes, and respiratory system; handle with caution

Upstream product

• 769-42-6 1,3-dimethylbarbituric acid 
• 100-52-7 benzaldehyde 
• 15018-52-7 5-benzyl-1,3-dimethyl-pyrimidine-2,4,6-trione 
• 62-53-3 aniline 
• 538-51-2 benzylidene phenylamine 
• 57270-81-2 5-(4-dimethylamino-benzylidene)-1,3-dimethyl-pyrimidine-2,4,6-trione 
• 57270-84-5 1,3-dimethyl-5-(4-methyl-benzylidene)-pyrimidine-2,4,6-trione 
• 783-08-4 [4-(benzylideneamino)phenyl]methanol 
• 780-25-6 N-benzylidene benzylamine 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 108-99-6 3-Methylpyridine 
• 100-11-8 1-bromomethyl-4-nitro-benzene 
• 70-11-1 α-bromoacetophenone 
• 616-47-7 1-methyl-1H-imidazole 

Downstream Products

• 15018-52-7 5-benzyl-1,3-dimethyl-pyrimidine-2,4,6-trione 
• 84333-06-2 5,7-Dimethyl-3-phenyl-2,7-dihydro-pyrazolo[3,4-d]pyrimidine-4,6-dione 
• 209798-63-0 7,7-bis(dimethylamino)-6,6-difluoro-1,3-dimethyl-5-phenyl-1,3,4,5,6,7-hexahydro-2H-pyrano[2,3-d]pyrimidine-2,4-dione 
• 934838-33-2 5-((1H-indol-3-yl)(phenyl)methyl)-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione 
• 35173-74-1 3,3'-bis-indolyl(phenyl)methane 
• 934838-38-7 C₂₂H₂₁N₃O₃ 
• 17371-59-4 2-methyl-3-((2-methyl-1H-indol-3-yl)(phenyl)methyl)-1H-indole 
• 1096157-71-9 2-benzoyl-7,9-dimethyl-1,4-diphenyl-7,9-diazaspiro[4.5]deca-1,3-diene-6,8,10-trione 
• 1185843-33-7 (5R)-1',3',7-trimethyl-5-phenyl-3,3a,5,6-tetrahydro-2H,2'H-spiro[1-benzothiophene-4,5'-pyrimidine]-2',4',6'(1'H,3'H)-trione 1,1-dioxide 
• 1185843-34-8 (5S)-1',3',7-trimethyl-5-phenyl-3,3a,5,6-tetrahydro-2H,2'H-spiro[1-benzothiophene-4,5'-pyrimidine]-2',4',6'(1'H,3'H)-trione 1,1-dioxide 
• 1260431-60-4 1,1',3,3'-tetramethyl-5-phenyl-1,5-dihydro-2H,2'H-spiro[furo[2,3-d]pyrimidine-6,5'-pyrimidine]-2,2',4,4',6'(1'H,3H,3'H)-pentaone 
• 1360568-30-4 dimethyl 1,3,4,7-tetrahydro-1,3-dimethyl-2,4-dioxo-5-phenyl-2H-pyrano[2,3-d]pyrimidine-6,7-dicarboxylate 
• 1360568-37-1 dimethyl (2E)-2-[(1,3-dimethyl-2,4,6-trioxotetrahydropyrimidin-5(2H)-ylidene)phenylmethyl]-2-butenedioate 

Relevant academic research and scientific papers

Supramolecular structures of five 5-(arylmethylene)-1,3-dimethyl- pyrimidine-2,4,6(1H,3H,5H)-triones: Isolated molecules, hydrogen-bonded chains and chains of fused hydrogen-bonded rings

In each of the five title compounds, namely 5-benzylidene-1,3- dimethylpyrimidine-2,4,6(1H,3H,5H)-trione, C13H12N 2O3, (I), 5-(3-methoxybenzylidene)-l,3-dimethylpyrimidine- 2,4,6(l/f,3H,5H)-trione, C14H14N2O4, (II), 5-(4-methoxybenzylidene)-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione, C14H14N2O4, (III), 5-[4-(dimethylamino)benzylidene]-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione, C15H17N3O3, (IV), and 5-(3,5-di-tert-butyl-4-hydroxybenzylidene)-1,3-dimethylpyrimidine-2,4,6(1H,3H, 5H)-trione, C21H28N2O4, (V), which crystallizes with Z′ = 2 in P1, there is a very wide C-C-C angle at the methine C atom linking the two rings, ranging from 137.1 (2)° in (I) to 139.14 (14)° in (III). There is evidence for intramolecular charge separation in (IV) and, to a lesser degree, in (III). The molecules of (I)-(III) are linked by pairs of C-H...O hydrogen bonds into chains of edge-fused rings, with alternating R22(14) and R2 2(16) rings in (I), alternating R22(14) and R44(20) rings in (II), with two types of R 22(16) rings alternating in (III). The molecules in (IV) are linked by a single C-H...O hydrogen bond into simple C(8) chains, but there are no direction-specific intermolecular interactions in (V).

A New Protocol for Catalyst-Free Regioselective Synthesis of 5,9-Dihydropyrimido[5,4- e ][1,2,4]triazolo[1,5- a ]pyrimidine-6,8(4 H,7 H)-diones

A novel, environmentally friendly synthesis of 5,9-dihydro-pyrimido[5,4-e][1,2,4]triazolo[1,5-a]pyrimidine-6,8(4H,7H)-diones has been developed by using a one-pot condensation of 1,3-dimethylbarbituric acid, 3-amino-1H-1,2,4-triazoles, and aromatic aldehydes. The reactions were established based on green chemistry principles under catalyst- and solvent-free conditions.

InCl3-Catalyzed, Three-Component Reactions for the Synthesis of Some Novel Functionalized/Annulated Barbituric Acids

Some novel 5-aminoalkylbarbituric acids and corresponding chromene derivatives were synthesized via a one-pot, three-component Mannich reaction starting from 1,3-dimethylbarbituric acid, arylaldehydes, and amines.

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.

Macrocyclic Modalities Combining Peptide Epitopes and Natural Product Fragments

"Hot loop" protein segments have variable structure and conformation and contribute crucially to protein-protein interactions. We describe a new hot loop mimicking modality, termed PepNats, in which natural product (NP)-inspired structures are incorporated as conformation-determining and-restricting structural elements into macrocyclic hot loop-derived peptides. Macrocyclic PepNats representing hot loops of inducible nitric oxide synthase (iNOS) and human agouti-related protein (AGRP) were synthesized on solid support employing macrocyclization by imine formation and subsequent stereoselective 1,3-dipolar cycloaddition as key steps. PepNats derived from the iNOS DINNN hot loop and the AGRP RFF hot spot sequence yielded novel and potent ligands of the SPRY domain-containing SOCS box protein 2 (SPSB2) that binds to iNOS, and selective ligands for AGRP-binding melanocortin (MC) receptors. NP-inspired fragment absolute configuration determines the conformation of the peptide part responsible for binding. These results demonstrate that combination of NP-inspired scaffolds with peptidic epitopes enables identification of novel hot loop mimics with conformationally constrained and biologically relevant structure.

Johnson-Corey-Chaykovsky fluorocyclopropanation of double activated alkenes: Scope and limitations

Johnson-Corey-Chaykovsky fluorocyclopropanation of double activated alkenes utilizing S-monofluoromethyl-S-phenyl-2,3,4,5-tetramethylphenylsulfonium tetrafluoroborate is an efficient approach to obtain a range of monofluorocyclopropane derivatives. So far, fluoromethylsulfonium salts have displayed the broadest scope for direct fluoromethylene transfer. In contrast to more commonly used fluorohalomethanes or freon derivatives, diarylfluoromethylsulfonium salts are bench stable, easy-to use reagents useful for the direct transfer of a fluoromethylene group to alkenes giving access to the challenging products-fluorocyclopropane derivatives. Interplay between the reactivity of the starting materials and stability of the fluorocyclopropanes formed determines the outcome of the process.

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.

PHOTOLABILE BARBITURATE COMPOUNDS

The present disclosure provides a redox initiator system for initiating polymerization comprising an oxidizing agent, a photolabile reducing agent derived from a barbiturate, and a transition metal complex that participates in a redox cycle. On exposure to actinic radiation, such as UV, the photolabile compound photolyzes, releasing the reducing agent and initiating the redox-initiated polymerization.

Direct Alkenylation of 2-Methylquinolines with Aldehydes through Synergistic Catalysis of 1,3-Dimethylbarbituric Acid and HOAc

An efficient and practical direct alkenylation of 2-methylquinolines with aldehydes has been achieved through a novel synergistic organocatalysis. The HOAc- activated 2-methylquiolines undergo a Michael addition to 1,3-dimethylbarbituric acid-activated aldehydes, followed by a retro-Michael addition to release 1,3-dimethylbarbituric acid and the target products. The transformation produced various 2-alkenylquinolines with good to excellent yields and featured mild reaction conditions, atom- and step-economy, good functional group tolerance, and operational simplicity. (Figure presented.).