The pyrazine ring is part of many polycyclic compounds of biological or industrial significance. Laurents method was vague, however, more than fifty years later, the compound was proved to be tetraphenylpyrazine30. Alkyl pyrazine synthesis via an open heated bath with. Pdf chemoenzymatic synthesis of pyrazines and pyrroles. With 2cyanopyrazine as the raw material, by adding a sodium hypochlorite solution and alkali, 2aminopyrazine is prepared through reaction, then 2amino3,5dibromopyrazine is obtained through bromination reaction, and 2amino5bromine3morpholinopyrazine, 2. Free radical formation from secondary amines in the maillard reaction. In the staedelrugheimer pyrazine synthesis 1876 2chloroacetophenone is reacted with ammonia to the amino ketone, then condensed and then oxidized to. Synthesis of pyrazine substituted 1,3,4thiadiazole. Ijms free fulltext design, synthesis, and cytotoxic. Pyrazine, any of a class of organic compounds of the heterocyclic series characterized by a ring structure containing four atoms of carbon and two of nitrogen. Some of these are among the oldest synthesis reactions still in use. A synthesis of symmetrical and unsymmetrical pyrazines.
Various substituted ketones were compatible for this transformation. Journal of agricultural and food chemistry 1997, 45 7, 242418. Pyrazinamide, itself a pyrazine derivative, along with rifampin and ethambutol, constitute firstline drugs for tuberculosis therapy. Design, synthesis, and in vitro activity of pyrazine compounds.
Apart from its numerous biological activities like antidiabetic, antiinflammatory, antimicrobial, pyrazine moiety plays an important role in luminescent materials. The invention discloses a preparation method of a pyrazine derivative, namely 3amino63, 5dimethylphenyl pyrazine2carboxamide. Synthesis of 2,3dicyanopyrazine and ethyl 5amino4,6. The majority of these derivatives showed much stronger cytotoxic activity than he. A chemical structure of all the new compounds was confirmed by 1 h nmr and mass spectral data. Pyrazine derivatives are known for antitumor, antibiotic, anticonvulsant, antituberculosis and diuretic activities, as well as kinase, enzymatic, and potent tubulin and ftsz polymerization inhibition. Greener approach toward one pot route to pyrazine synthesis. The design, synthesis, and characterization of a new pyrazinebased ditopic platinumii organometallic complex are reported. Hederagenin he is a novel triterpene template for the development of new antitumor compounds.
Many methods exist for the organic synthesis of pyrazine and its derivatives. Wed like to understand how you use our websites in order to improve them. Growth and angiogenesis are inhibited in vivo in developing. The invention relates to a preparation method of 2aminopyrazine derivatives, and belongs to the technical field of organic synthesis. The reaction provides highly substituted pyrazines in. Catalytic vapor phase oxidation of 2,5dimethylpyrazine gave 5methylpyrazine2aldehyde and pyrazine 2,5dialdehyde. Chemical properties of pyrazine cas 290379 download as pdf file download as excel file download as 2d mole file predict. Permission is granted to copy, distribute andor modify this document under the terms of the gnu free documentation license, version 1. Chemoenzymatic synthesis of pyrazines and pyrroles. This combination allows the convenient preparation of thieno3,4bpyrazine. Design, synthesis and antitumor activity of triterpenoid. Cn104387331a preparation method of pyrazine derivative. Synthesis, structure, physical properties and oled.
Xray absorption fine structure experiments elucidated that the cuii species 5. Compound 5 on deprotection with 4 m methanolic in meoh gave compound 6 as yellow colored hydrochloride salt with a 45% yield. A study is made of the deamination of diethylenetriamine over acidalkali catalysts, i. Synthesis, structure, physical properties and oled application of pyrazinetriphenylamine fused conjugated compounds liang xu, a yongbiao zhao, b guankui long, a yue wang, c jun zhao, d dongsheng li, d junbo li, a rakesh ganguly, e yongxin li, e handong sun, c xiao wei sun b and qichun zhang ad.
This combination allows the convenient preparation of thieno3,4b pyrazine. In the staedelrugheimer pyrazine synthesis 1876 2chloroacetophenone is reacted with ammonia to the amino ketone, then condensed and then oxidized to a pyrazine. Design, synthesis and antitumor activity of triterpenoid pyrazine derivatives from 23hydroxybetulinic acid hengyuan zhang a, b, yiwei wang a, b, peiqing zhu a, b, jie liu a, c, shengtao xu a, b, hequan yao a, b, jieyun jiang d, wencai ye e, xiaoming wu a, b, jinyi xu a, b, a. Borneo journal of resource science and technology 2017 72. Promoters which raise the acidity of the catalyst, affect the formation of triethylene diamine favorably. Pdf on jan 8, 2011, martin dolezal and others published synthesis and evaluation of pyrazine derivatives with herbicidal activity find. In lieu of an abstract, this is the articles first page. Pyrazine appeared to impair cam and embryo growth by inhibiting cell proliferation, since dna synthesis was significantly decreased by pyrazine. Pyrazine and its derivatives were also produced in industries mainly for fragrance, flavor and pharmaceutical applications. Alkyl pyrazine synthesis via an open heated bath with variable sugars, ammonia, and various amino acids. The loaels, noaels, and efficacy maximum percentage of inhibition for each compound tested in this study are compared in table 1 for the cam and embryo assays. Preliminary mechanistic investigations indicated that radical species were involved. Synthesis and catalytic oxidation of 2,5dimethylpyrazine. A general synthetic route has been developed for the efficient preparation of 2,3disubstituted thieno3,4bpyrazines.
Maillard product in the staedelrugheimer pyrazine synthesis 1876 2chloroacetophenone is reacted with ammonia to the amino ketone, then condensed and then oxidized to a pyrazine a variation is the gutknecht pyrazine synthesis 1879 also based on this selfcondensation but differing in the way the alphaketoamine is synthesised the chlorine. Pyrazine is a diazine that is benzene in which the carbon atoms at positions 1 and 4 have been replaced by nitrogen atoms. Pyrazine is a maillard product in the staedelrugheimer pyrazine synthesis 1876 2chloroacetophenone. Synthesis and characterization of pyrazine2carbohydrazide. Pyrazines heterocyclic building blocks sigmaaldrich. We focus herein on the synthesis of pyrazine derivatives with aliphatic or alicyclic side chains and their antimycobacterial, antibacterial, antifungal and pet. Synthesis and evaluation of pyrazine derivatives with herbicidal activity. A catalystfree arbuzovtype synthesis gave 21hpyrazinone phosphonates such. Synthesis and luminescence modulation of pyrazinebased gold. Exploration of pyrazineembedded antiaromatic polycyclic. Pyrazine 290379 buy and find out price and availability, msds, properties of tcis high quality specialty chemicals. Amino diol 3e was readily prepared by taguchis procedure, 8 combining cyclohexene oxide and aqueous ammonia. The reaction provides highly substituted pyrazines in good to excellent yields.
Its role in luminescent materials is due to its highly electron deficient nature specially when it is in the centre along the mainstay of extended. These methods eliminate problems in the preparation of the precursor 3,4diaminothiophene and utilize. The systematic study of pyrazine series of compounds was. Catalytic vapor phase oxidation of 2,5dimethylpyrazine gave 5methylpyrazine2aldehyde and pyrazine2,5dialdehyde. Synthesis and characterization of novel iminobenzoates with. Molecules free fulltext new potentially active pyrazinamide. Pyrazine being an aromatic compound can be represented as a resonance hybrid of a number of canonical structures. Higher temperatures and higher concentrations of glucose caused a decrease in the yield of pyrazines. Pdf synthesis and evaluation of pyrazine derivatives with. The molecular structure of the organoplatinum pyrazine dipod was determined by singlecrystal xray crystallography. The new compounds were screened for their anticonvulsant activity against maximal electroshock.
Coppercatalyzed aerobic oxidative chnh coupling between simple ketones and diamines was developed toward the synthesis of a variety of pyrazines. These metrics are regularly updated to reflect usage leading up to the last few days. A variation is the gutknecht pyrazine synthesis 1879 also based on this selfcondensation, but differing in the way the alphaketoamine is. Citations are the number of other articles citing this article, calculated by crossref and updated daily. The classical method for obtaining 2,5dimethylpyrazine by cyclization of aminoacetone has been improved by use of ammonium persulfate in place of mercuric chloride in the stage of catalytic oxidation of 2,5dimethyldihydropyrazine. The synthesis of 5 and 6 started with an s n ar reaction on the boc protected biphenyl intermediate 4 with lprolinol 17 and which provided the pyrazine ortho prolinol compound 5 with a 60% yield. This amino diol provided a fine platform for the elucidation of oxidation strategies.
A series of pyrazine2carbohydrazide derivatives has been synthesized and assessed for their in vitro antimicrobial activity against grampositive and gramnegative strains of bacteria. Synthesis of pyrazines 2ac and ethyl biphenyl3carboxylates 3ac. Pyrazine derivatives from chemical group 24 opinion of the scientific panel on food additives, flavourings, processing aids and materials in contact with food afc 1 view page or view pdf. Pyrazines have also been used as pharmaceutical intermediates, for example, 2methylpyrazine has been used for the synthesis of the antitubercular drug pyrazinamide. Increasing the amount of additive increases the amount of triethylenediamine, and cuts the optimum temperature at which it is formed. Article views are the countercompliant sum of full text article downloads since november 2008 both pdf and html across all institutions and individuals. The synthesis of new pyrazine substituted 1,3,4thiadiazole derivatives was carried out in good yield by the reaction of pyrazine substituted 1,3,4thiadiazoles with various sulfonyl chlorides. A series of pyrazine 2carbohydrazide derivatives has been synthesized and assessed for their in vitro antimicrobial activity against grampositive and gramnegative strains of bacteria. The pharmacodynamic properties of substituted amino pyrazines as well as their importance in the synthesis of pteridine and other polyfused heterocyclic systems is well known4,5. A new method of pyrazine synthesis for flavor use journal of. The yield of synthesized pyrazines increased at higher temperatures. Similarly, new liquid crystalline compounds are being made. Review on the synthesis of pyrazine and its derivatives.
Procedure for synthesis of pyrazine 2carbohydrazide ph 114 general procedure a solution of aromaticsubstituted aldehyde 0. We carried out our initial investigations with 2,2. Synthesis and luminescence modulation of pyrazinebased goldiii pincer complexes julio fernandezcestau, a benoit bertrand, a maria blaya, a garth a. Synthesis, structure, and vibrational spectrum of poly. Pyrazine medical definition merriamwebster medical dictionary. The invention discloses a preparation method of a pyrazine derivative, namely 3amino63, 5dimethylphenyl pyrazine 2carboxamide. Synthesis and reactions of some pyrazine derivatives. Review on the synthesis of pyrazine and its derivati ves.
Sep 15, 2016 the greatest total amount of pyrazines obtained was 17 280 g of extracted product which translated into 31% 2,6. Pyrazines are volatile compounds that are also of interest to the cosmetic, food, flavor. Catalytic synthesis of pyrazine, piperazine, and 1,4diaza2. Chebi 2, 5dimethylpyrazine is found in cereals and cereal products.