7391-61-9

Usage

InChI:InChI=1/C8H12N2O3/c1-4-5-6(11)9(2)8(13)10(3)7(5)12/h5H,4H2,1-3H3

Upstream product

• 77-78-1 dimethyl sulfate 
• 769-42-6 1,3-dimethylbarbituric acid 
• 109-89-7 diethylamine 
• 121-44-8 triethylamine 
• 58713-03-4 5-acetyl-1,3-dimethyl-2,4,6-trioxo-1,3-diazine 
• 64-17-5 ethanol 
• 74-96-4 ethyl bromide 
• 75-03-6 ethyl iodide 
• 96-31-1 N,N'-Dimethylurea 
• 601-75-2 ethylmalonic acid 
• 133-13-1 ethyl diethyl malonate 

Relevant academic research and scientific papers

Solvation and nucleophilic reactivity of conjugate-base anions of 5-methyl Meldrum's acid and of 3,3-dimethylbarbituric acid in acetonitrile-methanol

Conjugate-base anions of 5-methyl Meldrum's acid and of 1,3-dimethylbarbituric acid give comparable nucleophilic reactivity toward ethyl iodide in acetonitrile and also have specific interaction enthalpies, ΔtHSIAN→MeOH comparable with those of 3,5-dinitrobenzoate ion and of phthalimidide ion, while pKa values in the aqueous phase vary significantly among the series. The results lend support to the view that nucleophilic reactivity in acetonitrile is controlled mainly by the partial desolvation of nucleophilic anions accompanying activation. Variation of the specific interaction enthalpy for the present reactions on going from the initial to the transition-state is much smaller by comparison to those for imidide ion and carboxylate ion reactions. Theoretical analysis of the enthalpy with use of MNDO/PM3 procedures indicates that the steric inhibition of the approaching solvent molecule to the carbonyl oxygen by the group coordinated to the central atom is the main factor bringing about the smaller variation.

Method for preparing barbituric acid hydrocarbylation derivative by using ferrous complex

The invention relates to a method for preparing a barbituric acid hydrocarbylation derivative by using a ferrous complex, which comprises the steps of carrying out coupling reaction at room temperature by using barbituric acid and alcohol as raw materials and the ferrous complex containing an ortho-carboryl benzothiazole structure as a catalyst to prepare the barbituric acid hydrocarbylation derivative. Compared with the prior art, the method has the advantages that the ferrous complex containing the ortho-carboryl benzothiazole structure is applied to catalysis of coupling reaction of barbituric acid and alcohol, the barbituric acid hydrocarbylation derivative is prepared by a one-pot method, the barbituric acid hydrocarbylation derivative is synthesized by using simple, easily available and cheap raw materials at room temperature, and the method has the advantages of low catalyst use equivalent, mild reaction conditions, high substrate universality and high yield.

Method for synthesizing 5-substituted barbituric acid derivative under catalysis of rare earth chloride

The invention belongs to the technical field of synthetic chemistry, and particularly relates to a method for synthesizing a 5-substituted barbituric acid derivative under the catalysis of a rare earth chloride. The preparation method comprises: dissolving a halogenated hydrocarbon and 1,3-dimethyl barbituric acid in an organic solvent, carrying out a reaction for 6-10 h at a room temperature by using a rare earth chloride as a catalyst, and separating and purifying to obtain the 5-substituted barbituric acid derivative. According to the invention, the method has characteristics of simple andenvironmentally-friendly synthesis process, excellent selectivity, high yield and wide substrate range, and further has wide application value in the fields of biology, pharmaceutical chemistry industry and the like.

MELDRUM 'S ACID, BARBITURIC ACID AND PYRAZOLONE DERIVATIVES SUBSTITUTED WITH HYDROXYLAMINE AS HNO DONORS

The disclosed subject matter provides certain N-substituted hydroxylamine derivative compounds, pharmaceutical compositions and kits comprising such compounds, and methods of using such compounds or pharmaceutical compositions. In particular, the disclosed subject matter provides methods of using such compounds or pharmaceutical compositions for treating, preventing, or delaying the onset and/or development of a disease or condition. In some embodiments, the disease or condition is selected from cardiovascular diseases, ischemia, reperfusion injury, cancerous disease, pulmonary hypertension and conditions responsive to nitroxyl therapy.

Sequential one-pot bimetallic Ir(III)/Pd(0) catalysed mono-/bis-alkylation and spirocyclisation processes of 1,3-dimethylbarbituric acid and allenes

Microwave assisted indirect functionalization of alcohols with 1,3-dimethylbarbituric acid followed by spirocyclisation employing a sequential one-pot Ir(iii)/Pd(0) catalysed process, involving the formation of three new C-C bonds, one spirocyclic ring and one di- or tri-substituted exocyclic alkene, is described. The Royal Society of Chemistry.

Mono C-alkylation and mono C-benzylation of barbituric acids through zinc/acid reduction of acyl, benzylidene, and alkylidene barbiturate intermediates

Through systematic exploration of reaction conditions, very efficient preparative procedures for obtaining large quantities of substituted 5-alkyl and 5-benzylbarbituric acids were developed. The procedure involves a two step preparation in which the second step is zinc dust/acid reduction. For preparation of 5-alkylbarbiturates, the first step is the preparation of either 5-acyl or 5-alkylidenebarbiturate. If 5-benzylbarbiturate is the target product, then the first step includes the preparation of 5-benzylidene. Regardless of the nature of the first step, all reactions presented synthetic yields around 90% and isolation and purification involves only crystallization.

Relative reactivity of methyl iodide to ethyl iodide in nucleophilic substitution reactions in acetonitrile and partial desolvation accompanying activation

Through the examination of empirical correlations involving activation parameters for nucleophilic substitution of methyl iodide and of ethyl iodide, nucleophiles have been classified into three series: (1) nucleophiles with two equivalent reaction sites, (2) nucleophiles with a chlorine atom in the para-position, and (3) nucleophiles with a single reaction site. Three types of partial desolvation processes accompanying activation have been deduced on the basis of these classifications. A major factor determining the relative reactivity of methyl iodide to ethyl iodide in the substitution reaction of an anionic nucleophile having a single reaction site in acetonitrile (kMeI/kEtI) is suggested to be partial desolvation around the nucleophilic center on going from reactant to transition-state.

Reaction of 1,3-Dialkylbarbituric acids with aliphatic amines

On heating triethylammonium 1,3-dimethylbarbiturate, 1,3-dimethylthiobarbiturate, and 1,3-diphenylbarbiturate occurs dealkylation of triethylamine to afford in high yields the corresponding 5-ethyl substituted barbituric acids. The cleavage of alkyl groups happened also efficiently with tributyl, tribenzyl, and dimethylbenzylammonium salts, and less efficiently with trimethylammonium and diethylammonium salts. These reactions are characteristic only of 1.3-disubstituted barbituric acids; the barbituric acid and its 1-alkyl derivatives under these conditions suffer degradation.

Cpecificy of Metylation by Dimethyl Sulfate of Barbituric Acid Salts and Alkyl Derivatives

Metylation of mono- and dianionic forms of barbituric acid, its C- and N-alkyl derivatives with dimethylsulfate is studied. The methylation of monoanions occurs at the C5 carbon or O4(6) oxygen atoms, while that of dianions presumably at N1(3) nitrogen atoms. The selectivity of the dianions metylation at the nitrogen atoms increases in going from potassium to sodium and even more to lithium salts.

ALKYLATION OF 1,3-DIMETHYLBARBITURIC ACID BY ALKYL IODIDES

The alkylation of 1,3-dimethylbarbituric acid by methyl iodide, ethyl iodide, and isopropyl iodide in the presence of triethylamine was investigated.The kinetics of the process were studied, and it was shown that the steric and electronic factors affect the rate of the alkylation reactions.Only the products from alkylation at the C5 atom are formed in the case of methyl iodide, and concurrent alkylation at the C5 and O4(6) atoms is observed with ethyl iodide and isopropyl iodide.