123-32-0Relevant articles and documents
One-pot synthesis of 2-hydroxymethyl-5-methylpyrazine from renewable 1,3-dihydroxyacetone
Song, Lei,Zheng, Mingyuan,Pang, Jifeng,Sebastian, Joby,Wang, Wentao,Qu, Minjie,Zhao, Jian,Wang, Xinhong,Zhang, Tao
, p. 3515 - 3519 (2017)
An efficient and green method for the synthesis of 2-hydroxymethyl-5-methylpyrazine was achieved from biomass derived 1,3-dihydroxyacetone and diammonium phosphate via a one-pot reaction. The product yield was as high as 72% under optimized conditions of pH = 8.0-9.1 at 90 °C for 1 hour in a dioxane and water mixture as a solvent. A possible reaction mechanism was proposed according to the reaction kinetics, NMR and in situ ATR-IR characterization studies.
Aminoacetone oxidase from Streptococcus oligofermentans belongs to a new three-domain family of bacterial flavoproteins
Molla, Gianluca,Nardini, Marco,Motta, Paolo,D'Arrigo, Paola,Panzeri, Walter,Pollegioni, Loredano
, p. 387 - 399 (2014)
The aaoSogene from Streptococcus oligofermentans encodes a 43 kDa flavoprotein, aminoacetone oxidase (SoAAO), which was reported to possess a low catalytic activity against several different L-amino acids; accordingly, it was classified as an L
SYNTHESIS AND CATALYTIC OXIDATION OF 2,5-DIMETHYLPYRAZINE
Kastron, V.V.,Iovel', I.G.,Skrastyn'sh, I.P.,Gol'dberg, Yu.Sh.,Shimanskaya, M.V.,Dubur, G.Ya.
, p. 915 - 917 (1986)
The classical method for obtaining 2,5-dimethylpyrazine by cyclization of aminoacetone has been improved by use of ammonium persulfate in place of mercuric chloride in the stage of catalytic oxidation of 2,5-dimethyldihydropyrazine.Catalytic vapor phase oxidation of 2,5-dimethylpyrazine gave 5-methylpyrazine-2-aldehyde and pyrazine-2,5-dialdehyde.
Comparison of pyrazines formation in methionine/glucose and corresponding Amadori rearrangement product model
Cui, Heping,Deng, Shibin,Hayat, Khizar,Ho, Chi-Tang,Zhai, Yun,Zhang, Qiang,Zhang, Xiaoming
, (2022/03/07)
The generation of pyrazines in a binary methionine/glucose (Met/Glc) mixture and corresponding methionine/glucose-derived Amadori rearrangement product (MG-ARP) was studied. Quantitative analyses of pyrazines and methional revealed that MG-ARP generated more methional compared to Met/Glc, whereas lower content and fewer species of pyrazines were observed in the MG-ARP model. Comparing the availability of α-dicarbonyl compounds generated from the Met/Glc model, methylglyoxal (MGO) was a considerably effective α-dicarbonyl compound for the formation of pyrazines during MG-ARP degradation, but glyoxal (GO) produced from MG-ARP did not effectively participate in the corresponding formation of pyrazines due to the asynchrony on the formation of GO and recovered Met. Diacetyl (DA) content was not high enough to form corresponding pyrazines in the MG-ARP model. The insufficient interaction of precursors and rapid drops in pH limited the formation of pyrazines during MG-ARP degradation. Increasing reaction temperature could reduce the negative inhibitory effect by promoting the content of precursors.
Characteristic flavor formation of thermally processed N-(1-deoxy-α-D-ribulos-1-yl)-glycine: Decisive role of additional amino acids and promotional effect of glyoxal
Zhan, Huan,Cui, Heping,Yu, Junhe,Hayat, Khizar,Wu, Xian,Zhang, Xiaoming,Ho, Chi-Tang
, (2021/09/28)
The role of amino acids and α-dicarbonyls in the flavor formation of Amadori rearrangement product (ARP) during thermal processing was investigated. Comparisons of the volatile compounds and their concentrations when N-(1-deoxy-α-D-ribulos-1-yl)-glycine r
Ir-Catalyzed Reversible Acceptorless Dehydrogenation/Hydrogenation of N-Substituted and Unsubstituted Heterocycles Enabled by a Polymer-Cross-Linking Bisphosphine
Zhang, Deliang,Iwai, Tomohiro,Sawamura, Masaya
supporting information, p. 5240 - 5245 (2020/07/03)
The polystyrene-cross-linking bisphosphine ligand PS-DPPBz was effective for the Ir-catalyzed reversible acceptorless dehydrogenation/hydrogenation of N-heterocycles. Notably, this protocol is applicable to the dehydrogenation of N-substituted indoline derivatives with various N-substituents with different electronic and steric natures. A reaction pathway involving oxidative addition of an N-adjacent C(sp3)-H bond to a bisphosphine-coordinated Ir(I) center is proposed for the dehydrogenation of N-substituted substrates.
Acceptorless Dehydrogenative Coupling Using Ammonia: Direct Synthesis of N-Heteroaromatics from Diols Catalyzed by Ruthenium
Daw, Prosenjit,Ben-David, Yehoshoa,Milstein, David
supporting information, p. 11931 - 11934 (2018/09/27)
The synthesis of N-heteroaromatic compounds via an acceptorless dehydrogenative coupling process involving direct use of ammonia as the nitrogen source was explored. We report the synthesis of pyrazine derivatives from 1,2-diols and the synthesis of N-substituted pyrroles by a multicomponent dehydrogenative coupling of 1,4-diols and primary alcohols with ammonia. The acridine-based Ru-pincer complex 1 is an effective catalyst for these transformations, in which the acridine backbone is converted to an anionic dearomatized PNP-pincer ligand framework.
Synthesis of Pyrazines and Quinoxalines via Acceptorless Dehydrogenative Coupling Routes Catalyzed by Manganese Pincer Complexes
Daw, Prosenjit,Kumar, Amit,Espinosa-Jalapa, Noel Angel,Diskin-Posner, Yael,Ben-David, Yehoshoa,Milstein, David
, p. 7734 - 7741 (2018/08/03)
Base-metal catalyzed dehydrogenative self-coupling of 2-amino alcohols to selectively form functionalized 2,5-substituted pyrazine derivatives is presented. Also, 2-substituted quinoxaline derivatives are synthesized by dehydrogenative coupling of 1,2-diaminobenzene and 1,2-diols. In both cases, water and hydrogen gas are formed as the sole byproducts. The reactions are catalyzed by acridine-based pincer complexes of earth-abundant manganese.
Reversible Interconversion between 2,5-Dimethylpyrazine and 2,5-Dimethylpiperazine by Iridium-Catalyzed Hydrogenation/Dehydrogenation for Efficient Hydrogen Storage
Fujita, Ken-Ichi,Wada, Tomokatsu,Shiraishi, Takumi
supporting information, p. 10886 - 10889 (2017/08/30)
A new hydrogen storage system based on the hydrogenation and dehydrogenation of nitrogen heterocyclic compounds, employing a single iridium catalyst, has been developed. Efficient hydrogen storage using relatively small amounts of solvent compared with previous systems was achieved by this new system. Reversible transformations between 2,5-dimethylpyrazine and 2,5-dimethylpiperazine, accompanied by the uptake and release of three equivalents of hydrogen, could be repeated almost quantitatively at least four times without any loss of efficiency. Furthermore, hydrogen storage under solvent-free conditions was also accomplished.
Vapor phase phototransposition chemistry of dimethylpyrazines and dimethylpyrimidines
Pavlik, James W.,Vongakorn, Tharinee,Kebede, Naod
, p. 216 - 228 (2017/11/17)
Based on their phototransposition chemistry, the three dimethylpyrazines and four dimethylpyrimidines can be arranged into two groups. 2,5-Dimethylpyrazine, 2,5-dimethylpyrimidine, and 4,6-dimethylpyrimidine constitute a photochemical triad. Irradiation of any one member of the triad in the vapor phase results in the formation of the other two members. The other four isomers, 2,6-dimethylpyrazine, 2,3-dimethylpyrazine, 2,4- dimethylpyrimidine, and 4,5-dimethylpyrimidine constitute a photochemical tetrad. Irradiation of any one member results in the formation of the other three. In addition, 2,4-dimethylpyrimidine and 2,6-dimethylpyrazine also photoisomerize to 3,6-dimethylpyridazine. Irradiation of the last in the vapor state resulted in the four members of the tetrad.
