2962-90-5

Usage

Family

Pteridine family

Type of Compound

Heterocyclic compound

Structure

Tricyclic structure

Derivation

Derived from pteridine

Role in Synthesis

Important in the synthesis of tetrahydrobiopterin

Coenzyme Involvement

Tetrahydrobiopterin is a coenzyme involved in the production of neurotransmitters

Neurotransmitters

Dopamine and serotonin

Additional Synthesis

Involved in the synthesis of nitric oxide

Potential Applications

Treatment of neurological disorders

Specific Disorders

Phenylketonuria and Parkinson's disease

Upstream product

• 2757-85-9 1,3-dimethylalloxan 
• 39145-59-0 o-phenylenediamine hydrochloride 
• 858478-70-3 methyl-(3-methylcarbamoyl-quinoxalin-2-yl)-carbamic acid ethyl ester 
• 186581-53-3 diazomethane 
• 490-59-5 alloxazine 
• 77-78-1 dimethyl sulfate 
• 73817-31-9 1,3,10-trimethylalloxazinium trifluoroacetate 
• 15008-33-0 (5-bromopentyl)trimethylammonium bromide 
• 2758-06-7 (2-bromoethyl)trimethylammonium bromide 
• 49679-45-0 ethyl 3-chloroquinoxaline-2-carboxylate 
• 858478-56-5 3-methylamino-quinoxaline-2-carboxylic acid methylamide 
• 64267-60-3 4^a,10^a-ethylenedioxy-1,3,10-trimethyl-4^a,5,10,10^a-tetrahydroalloxazine 
• 1128-14-9 5-amino-6-chloro-1,3-dimethyluracil 
• 61541-41-1 6-azido-1,3-dimethylpyrimidine-2,4(1H,3H)-dione 

Relevant academic research and scientific papers

ACTIVATION AND TRANSFER OF OXYGEN-XVI. SPONTANEOUS ELECTRON TRANSFER IN FLAVINIUM SALT SOLUTIONS. A NEW PRINCIPLE FOR THE DEVELOPMENT OF OXYGEN ACTIVATION MODELS

Blue coloured 10,10a-ring opened intermediates 5a,5b arising in the autoxidation of a dihydroflavin model (Scheme 1) are also formed on proper treatment of some N1-alkylflavinium salts 7 (Scheme 2).The conditions giving optimal 10,10a-ring opening have been determined (Figs. 1-2).The flavinium salts (RFlox+, A-) show spontaneous electron transfer in the dark, producing a flavosemiquinone (RFl.) and a counter-radical, probably a radical cation (RFl-A+.) derived from a flavin adduct (pathway b, Scheme 3).The formation of a neutral, unstable 1-RFl. appeared from the spontaneous N10-dealkylation (pathway d2) competing with the O2-activation (pathway c1).A generation of CO2 may occur wich indicates the formation of an unstable acyloxy radical (A.) by a decomposition of RFl-A+. (pathway d3).Cl3CCOO- can even be catalytically decomposed by RFlox+.This proves that RFlox+ is recycled from the RFl.-state also (pathway d1) for wich O2 is not a prerequisite.On the other hand, Cl3CCOO- is "repaired" under conditions giving a 10,10a-ring opening (Fig 3).The preservation of the acid anion and the results of the O2-balance are consistent with the conclusion that the 10,10a-ring opening is coupled with or followed by an electron transfer from a peroxy radical to RFl-A+. giving a generation of O2 (Scheme 4).A 10,10a-ring opened hydroperoxide 5a (XH=OOH; Scheme 1) is proposed to be the result of a similar one-electron transfer reaction (A=OOH; Scheme 4).

Flavin Derivatives with Tailored Redox Properties: Synthesis, Characterization, and Electrochemical Behavior

This study establishes structure–property relationships for four synthetic flavin molecules as bioinspired redox mediators in electro- and photocatalysis applications. The studied flavin compounds were disubstituted with polar substituents at the N1 and N

Electron-deficient alloxazinium salts: Efficient organocatalysts of mild and chemoselective sulfoxidations with hydrogen peroxide

A series of substituted alloxazinium perchlorates has been prepared and tested as catalysts for the oxidation of sulfides to sulfoxides with hydrogen peroxide. The logarithms of the observed rate constants of thioanisole oxidation correlate with the Hammett σ constants of the substituents on the alloxazinium catalysts, as well as with their reduction potentials E 0′ and their pKR+ values, representing the alloxazinium salt/pseudobase equilibrium. The stronger the electron-withdrawing substituent, the more efficient is the alloxazinium catalyst. The alloxazinium salts with a cyano or trifluoromethyl group in position 8 proved to be the most efficient, operating at room temperature at small loadings, down to 0.1 mol%, achieving turnover number values of up to 640 and acceleration by a factor of 350 relative to the non-catalyzed oxidation. The 8-cyanoalloxazinium perchlorate was evaluated as the best catalyst; however, due to its relatively good accessibility, the 8-(trifluoromethyl)alloxazinium perchlorate seems to be the catalyst of choice for sulfoxidations with hydrogen peroxide. It was successfully tested for the sulfoxidation of a series of aliphatic and aromatic sulfides on a preparative scale. It produced the corresponding sulfoxides in quantitative conversions and with high isolated yields (87-98%). No over-oxidation to sulfone was ever observed. Copyright

Organocatalytic Dakin oxidation by nucleophilic flavin catalysts

Flavin catalysts perform the first organocatalytic Dakin oxidation of electron-rich arylaldehydes to phenols under mild, basic conditions. Catechols are readily prepared, and the oxidation of 2-hydroxyacetophenone was achieved. Aerobic oxidation is displayed in the presence of Zn(0) as a reducing agent. This reactivity broadens the scope of biomimetic flavin catalysis in the realm of nucleophilic oxidations, providing a framework for mechanistic investigations for related oxidations, such as the Baeyer-Villiger oxidation and Weitz-Scheffer epoxidation.

Aerobic organocatalytic oxidation of aryl aldehydes: Flavin catalyst turnover by Hantzsch's ester

The first Dakin oxidation fueled by molecular oxygen as the terminal oxidant is reported. Flavin and NAD(P)H coenzymes, from natural enzymatic redox systems, inspired the use of flavin organocatalysts and a Hantzsch ester to perform transition-metal-free, aerobic oxidations. Catechols and electron-rich phenols are achieved with as low as a 0.1 mol % catalyst loading, 1 equiv of Hantzsch ester, and O2 or air as the stoichiometric oxidant source.

Synthesis and cyclization of novel lumazine - Enediyne chimeras

Lumazine derivatives (6-8), appended with ethynyl groups in positions 7 and 8, were synthesized and examined for their ability to undergo Bergman cyclization. Oxo compound (7) was found to give good yields of Bergman cyclization products (? 37 %), whereas the analogues (6) and (8) did not cyclize as efficiently or gave no identifiable cyclization products.

New Synthesis of Alloxazine Derivatives

Nitrosation of 6-anilino-1,3-dimethyluracils yields 1,3-dimethylalloxazine derivatives and the corresponding 5-oxides. Reduction of the N-oxides results in formation of the alloxazines. This reaction opens the way to difficultly accessible alloxazine deri

Mild and Efficient Flavin-Catalyzed H2O2 Oxidation of Tertiar Amines to Amine N-Oxides

A mild and highly effective H2O2 oxidation of tertiary amines has been developed by the use of flavin catalysis. Eight aliphatic amines were oxidized to their corresponding N-oxides in fast and selective reactions. For all substrates a considerable rate enhancement was observed compared to the noncatalyzed reactions. The product N-oxides were isolated in good yields using this mild oxidation system based on the environmentally attractive oxidant H2O2. As the catalyst, an N1N5- dialkylated flavin was used as an analogue of the biologically important flavin redox cofactor. The catalytic cycle proposed for the flavin catalysis accounts for the observation that, in addition to the hydrogen peroxide oxidant, molecular oxygen is required for the initiation of the process.

A NEW SYNTHESIS OF FERVENULINS AND ALLOXAZINES. THERMOLYSIS AND PHOTOLYSIS OF 6-AZIDO-1,3-DIMETHYLURACIL WITH TETRAZOLES AND BENZOTRIAZOLES

Thermolysis of 6-azido-1,3-dimethyluracil(1) in the presence of 5-substituted tetrazoles(2) gave 3-substituted fervenulins(4), which were also synthesized from the intermediates(3) prepared by photolysis of (1) with (2).Irradiation of (1) with benzotriazoles(6) in tetrahydrofuran gave 6-(benzotriazol-1-yl)uracils(7), which were irradiated in methanol to afford alloxazines (8).