21544-73-0

Upstream product

• 30537-82-7 betaine of 1,3-dimethyl-5-phenyliodoniobarbituric acid 
• 74808-90-5 5-diazo-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione 
• 30066-93-4 5-amino-1,3-dimethyl-pyrimidine-2,4,6-(1H,3H,5H)-trione 
• 5417-13-0 1,3-dimethylvioluric acid 
• 7732-18-5 water 
• 7782-50-5 chlorine 
• 10026-13-8 phosphorus pentachloride 
• 2835-45-2 amalic acid 
• 6972-27-6 1,3-Dimethyl-6-chlorouracil 
• 769-42-6 1,3-dimethylbarbituric acid 
• 58378-09-9 1,3,1',3'-tetramethylhydurilic acid 

Downstream Products

• 21991-30-0 5,5-dibenzyl-1,3-dimethyl-2,3,4(1H,3H,5H)pyrimidinetrione 
• 15018-52-7 5-benzyl-1,3-dimethyl-pyrimidine-2,4,6-trione 
• 14305-99-8 1,3-dimethyl-5-nitro-pyrimidin-2,4,6(1H,3H,5H)-trione 
• 5417-13-0 1,3-dimethylvioluric acid 
• 2757-85-9 1,3-dimethylalloxan 
• 769-42-6 1,3-dimethylbarbituric acid 

Relevant academic research and scientific papers

Nucleophilic substitution approach towards 1,3-dimethylbarbituric acid derivatives - New synthetic routes and crystal structures

We describe simple, convenient and high-yielding nucleophilic substitution reactions to synthesize new derivatives of 1,3-dimethylbarbituric acid (1a). Based on its active C5 position, condensing 1a with sulfuryl chloride gives the corresponding 5,5-dichloro-1,3-dimethylbarbituric acid (13). The latter was reacted with silver nitrite and potassium cyanide to afford 5-chloro-5-nitro-1, 3-dimethylbarbituric acid (14) and 5-cyano-1,3-dimethylbarbiturate (17), respectively. Furthermore, by employing the nucleophilic character of 2,3-dihydro-1,3-diisopropyl-4,5-dimethylimidazol-2-ylidene (8) the obtained compounds 13 and 14 have been converted to 2-chloro-1,3-diisopropyl-4,5- dimethyl-1H-imidazol-3-ium-1,3-dimethyl-5-nitro-1,3-dimethylbarbiturate (18) and 1,3-dimethylbarbituric acid trimer (21), respectively. X-ray structures for compounds 13, 14, 17, 18 and 21 were determined.

Geminal Dichlorination of Phenyliodonium Ylides of β-Dicarbonyl Compounds through Double Ligand Transfer from (Dichloroiodo)benzene

Pre-formed phenyliodonium ylides of cyclic and acyclic β-diketones, β-keto esters and β-diesters were reacted with (dichloroiodo)benzene, resulting in transfer of both chloride ligands onto the ylidic carbon. These two hypervalent iodine(III) compounds exhibit high reactivity towards each other under mild reaction conditions and typically afford the gem-dichloride products in good yield. Upon comparison of these chlorination reactions with those of the analogous diazocarbonyl compounds, reactions of iodonium ylides were unilaterally faster, and often gave the products in higher yield.

N-Chloro-N-methoxybenzenesulfonamide: A Chlorinating Reagent

A structurally simple and reactive chlorinating reagent, N-chloro-N-methoxybenzenesulfonamide, was conveniently and economically prepared in high yield. 1,3-Diketones, β-keto esters, benzoyl trifluoroacetones, phenols, anisoles, heteroarenes, and aromatic amines were successfully chlorinated, and the products were obtained in good to high yields.

Dichlorination of α-Diazo-β-dicarbonyls using (dichloroiodo)benzene

Abstract α-Diazo-β-dicarbonyl compounds were chlorinated using (dichloro)iodobenzene and an activating catalyst. A broad range of reaction rates was observed, which paralleled the relative stability/nucleo-philicity of the diazo compounds. Acyclic diazocarbonyls reacted faster than cyclics, and β-diketones were much faster to react than β-keto esters or β-diesters. Lewis acid activation was used for the first time, allowing us to overcome instances of poor chemoselectivity. Though the yields ranged from low to good, this chlorination reaction has again proven a mild and effective halogenation strategy.

CFBSA: a novel and practical chlorinating reagent

A structurally simple, highly reactive chlorinating reagent, N-chloro-N-fluorobenzenesulfonylamine (CFBSA), was conveniently prepared from inexpensive Chloramine B in high yield. A wide range of substrates were chlorinated with it to obtain products in good to high yields and appropriate selectivity.

An unprecedented study of the rearrangement of 5,5-diazidobarbituric acids under various conditions

The unexpected parabanic acid derivatives 6a,b were obtained via unprecedented rearrangement of 5,5-diazidobarbituric acids 2a,b upon stirring in water at 50-60°C. Themolysis of diazides 2a,b in benzyl alcohol at 120-130°C afforded the tetrazole derivative 11 and/or benzyl allophanate 14.