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einhorn brunner reaction wikipedia jump to content main menu main menu move to sidebar hide navigation main page contents current events random article about wikipedia contact us contribute help learn to edit community portal recent changes upload file special pages search search appearance donate create account log in personal tools donate create account log in contents move to sidebar hide top 1 regioselectivity 2 mechanism 3 applications 4 related reactions 5 references toggle the table of contents einhorn brunner reaction 7 languages deutsch español فارسی bahasa indonesia 日本語 nederlands 中文 edit links article talk english read edit view history tools tools move to sidebar hide actions read edit view history general what links here related changes upload file permanent link page information cite this page get shortened url switch to legacy parser print export download as pdf printable version in other projects wikimedia commons wikidata item appearance move to sidebar hide from wikipedia the free encyclopedia chemical reaction of imides with alkyl hydrazines the einhorn brunner reaction is the designation for the chemical reaction of imides with alkyl hydrazines to form an isomeric mixture of 1 2 4 triazoles it was initially described by the german chemist alfred einhorn in a paper published in 1905 describing n methylol compounds of amides 1 in 1914 chemist karl brunner published a paper expanding on einhorn s research of the reaction pictured below thus resulting in the naming as the einhorn brunner 2 substituted 1 2 4 triazole have been prepared from diverse imides and hydrazines 3 4 5 6 the einhorn brunner reaction regioselectivity edit in the case that the r groups of the imide are different the reaction has regioselectivity in their research on the synthesis of 1 2 4 triazoles potts determined that the strongest acidic group attached to the side of the imide will be favored for the 3 position on the triazole ring 5 in the diagram below if one considers the blue r group to be more acidic in respect to the green the favored product would be the isomer on the right mechanism edit for clarity in depicting the electron flow of the mechanism the image below only consists of one of the isomers generated in an einhorn brunner reaction the first step of the mechanism involves the protonating of the substituted nitrogen of the hydrazine 1 generating the cation 2 protonated hydrazine 2 protonates the oxygen of one of the carbonyl groups of the imide this allows for an attack on the electrophilic carbon of the protonated carbonyl group by the primary amino group of the hydrazine producing 3 the loss of water and subsequent generation of a double bond between the recently formed nitrogen carbon sigma bond results in the formation of iminiumion 4 4 undergoes a 1 5 proton shift from the nitrogen to the carbonyl oxygen seen in 5 intramolecular attack of the electrophilic carbonyl carbon by the nitrogen resulting in a 5 membered ring closure of the positively charged 6 elimination of a water group and then a proton results in the intermediates of 7 and 8 respectively and finally results in the formation of 9 one 1 2 4 triazole isomer 7 applications edit triazoles have been found to have a number of real world applications as antibacterial agents citation needed the einhorn brunner reaction maintains scientific importance and relevance in the production of 1 2 4 triazoles which can be further substituted for their medicinal value research done by pattan et al specifically on 1 2 4 triazoles found antibacterial antifungal antitubercular and anti inflammatory activity of variously substituted compounds 8 klimešová and colleagues also report antimycobacterial activity of 1 2 4 triazoles against tuberculosis but also risk a low level of toxicity 6 related reactions edit pellizzari reaction references edit alfred einhorn eduard bischkopff bruno szelinski gustav schupp eduard spröngerts carl ladisch theodor mauermayer 1905 ueber die n methylolverbindungen der säureamide justus liebig s annalen der chemie 343 2 3 207 305 229 doi 10 1002 jlac 19053430207 cite journal cs1 maint multiple names authors list link brunner karl 1914 eine neue darstellungsweise von sekundären säureamiden chemische berichte 47 3 2671 2680 doi 10 1002 cber 19140470351 karl brunner 1915 eine neue darstellungsweise von triazolen monatshefte für chemie 36 7 8 509 534 doi 10 1007 bf01524682 s2cid 94365050 m r atkinson j b polya 1954 triazoles part ii n substitution of some 1 2 4 triazoles journal of the chemical society 141 doi 10 1039 jr9540000141 1 2 potts k t 1961 the chemistry of 1 2 4 triazoles chemical reviews 61 2 87 127 doi 10 1021 cr60210a001 1 2 klimesová v zahajská l 2004 synthesis and antimycobacterial activity of 1 2 4 triazole 3 benzylsulfanyl derivatives il farmaco 59 4 279 288 doi 10 1016 j farmac 2004 01 006 pmid 15081345 wang z 2009 comprehensive organic name reactions 3 volume set john wiley sons p 971 isbn 9780471704508 pattan s gadhave p tambe v dengale s thakur d hiremath s v shete r v deotarse p jan 2012 synthesis and evaluation of some novel 1 2 4 triazole derivatives for antmicrobial antitubercular and anti inflammatory activities pdf indian journal of chemistry 51b 297 301 retrieved from https en wikipedia org w index php title einhorn brunner_reaction oldid 1343294946 categories heterocycle forming reactions name reactions hidden categories articles with short description short description matches wikidata cs1 maint multiple names authors list all articles with unsourced statements articles with unsourced statements from december 2019 this page was last edited on 13 march 2026 at 12 13 utc page was rendered with parsoid text is available under the creative commons attribution sharealike 4 0 license additional terms may apply by using this site you agree to the terms of use and privacy policy wikipedia is a registered trademark of the wikimedia foundation inc a non profit organization privacy policy 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