Synthesis of 5,7-dioxo-3-methyl-5,6,7,8-tetrahydropyrimido[5,4-e]-as-triazine

Zee-Cheng, Kwang-Yuen; Cheng, C. C.

doi:10.1021/jm00311a063

Cited by 12 publications

(3 citation statements)

References 4 publications

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“…[4]T 11) summarized in Table III and Figures 3 and 4 are in agreement with these expressions. Thus, under all conditions, the reaction is first order in the 02 concentration (Figure 3), at low [Cu(II)]T the reaction is third order overall (Table III), and at high concentrations of either Cu(II) or 4 the rate becomes independent of the concentration of that reactant (Figure 4).…”

Section: Discussionsupporting

confidence: 83%

Possible model reaction for some amine oxidases. Kinetics and mechanism of the copper(II)-catalyzed autoxidation of some diaminouracils

Al-Arab¹,

Hamilton²

1986

J. Am. Chem. Soc.

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Section: Discussionsupporting

confidence: 83%

Possible model reaction for some amine oxidases. Kinetics and mechanism of the copper(II)-catalyzed autoxidation of some diaminouracils

Al-Arab¹,

Hamilton²

1986

J. Am. Chem. Soc.

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“…We briefly examined a modification whereby the original S N Ar conditions (neat, 95–110°C, 3 hours) were replaced by microwave conditions (180°C, 10 minutes), but in our hands the yields topped out at about 16% prior to nitrosylation. We were accordingly drawn to an alternative route initially reported by Cresswell and Wood [ 31 ], whereby the displacement was carried out on the more highly activated nitrouracil 3b [ 40 ], which afforded 4c smoothly in very high yield, was stable indefinitely, and could be used without additional purification.…”

Section: Resultsmentioning

confidence: 99%

“…The syntheses of (2 R ,3 S ,4 S )-5-aminopentane-1,2,3,4-tetraol ( 2 ) [ 29 ], 6-chloro-5-nitropyrimidine-2,4(1 H ,3 H )-dione ( 3b ) [ 31 , 40 ], and 5-nitro-6-(((2 S ,3 S ,4 R )-2,3,4,5-tetrahydroxypentyl)amino)pyrimidine-2,4(1 H ,3 H )-dione ( 4c ) [ 31 ] were carried out by previously reported routes. They are included in Supporting Information S1 File along with full characterization of the intermediates.…”

Section: Methodsmentioning

confidence: 99%

Synthesis, stabilization, and characterization of the MR1 ligand precursor 5-amino-6-D-ribitylaminouracil (5-A-RU)

Vorkas

Chaudhry

et al. 2018

PLoS ONE

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Mucosal-associated invariant T (MAIT) cells are an abundant class of innate T cells restricted by the MHC I-related molecule MR1. MAIT cells can recognize bacterially-derived metabolic intermediates from the riboflavin pathway presented by MR1 and are postulated to play a role in innate antibacterial immunity through production of cytokines and direct bacterial killing. MR1 tetramers, typically stabilized by the adduct of 5-amino-6-D-ribitylaminouracil (5-A-RU) and methylglyoxal (MeG), are important tools for the study of MAIT cells. A long-standing problem with 5-A-RU is that it is unstable upon storage. Herein we report an efficient synthetic approach to the HCl salt of this ligand, which has improved stability during storage. We also show that synthetic 5-A-RU•HCl produced by this method may be used in protocols for the stimulation of human MAIT cells and production of both human and mouse MR1 tetramers for MAIT cell identification.

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Hydrocarbon Oxidation

Hobbs¹

2000

Kirk-Othmer Encyclopedia of Chemical Technology

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Hydrocarbon oxidation has long been a significant source of organic chemicals. Both vapor‐ and liquid‐phase reactions are of interest; they are believed to involve free‐radical chain mechanisms. Modern understanding of these reactions has developed over the last half of the twentieth century. Although sharp disputes are frequent, significant agreement on underlying principles is apparent. Vapor‐phase oxidations can be conveniently divided into low, middle, and high temperature ranges. Fundamental changes in mechanisms occur over these regions. The direct oxidation of methane to methanol, formaldehyde, and/or C 2 products has received intense study, but no viable processes have yet been developed. Most other studies in this area are directed toward fuel utilization and pollution abatement. Liquid‐phase oxidations of aliphatics have declined in importance as sources of bulk chemicals. However, the oxidation of butane to acetic acid, and of isobutane to t ‐butylhydroperoxide (to produce propylene oxide), and of cyclohexane to cyclohexanol and cycohexanone (to produce adipic acid and nylon), remain important industrial processes. Oxidations of alkylaromatics continue to be important industrially. The oxidation of p ‐xylene to terephthalic acid and cumene to phenol are dominant routes to these products. The potential for producing fine chemicals by such oxidations is developing rapidly.

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Synthesis of 5,7-dioxo-3-methyl-5,6,7,8-tetrahydropyrimido[5,4-e]-as-triazine

Cited by 12 publications

References 4 publications

Possible model reaction for some amine oxidases. Kinetics and mechanism of the copper(II)-catalyzed autoxidation of some diaminouracils

Possible model reaction for some amine oxidases. Kinetics and mechanism of the copper(II)-catalyzed autoxidation of some diaminouracils

Synthesis, stabilization, and characterization of the MR1 ligand precursor 5-amino-6-D-ribitylaminouracil (5-A-RU)

Hydrocarbon Oxidation

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