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davis beirut 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 mechanism in base 2 other variants of the davis beirut reaction 3 applications 4 references toggle the table of contents davis beirut reaction 2 languages فارسی தமிழ் 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 davis beirut reaction named after university of california davis american university of beirut reaction type ring forming reaction the davis beirut reaction is n n bond forming heterocyclization that creates numerous types of 2 h indazoles and indazolones in both acidic and basic conditions 1 2 3 4 5 the davis beirut reaction is named after mark kurth and makhluf haddadin s respective universities university of california davis and american university of beirut and is appealing because it uses inexpensive starting materials and does not require toxic metals 3 6 7 formation of 2 h indazoles by the davis beirut reaction mechanism in base edit davis beirut 2h indazoles mechanism the current proposed mechanism for the davis beirut reaction in base was first published in 2005 by kurth olmstead and haddadin the reaction occurs when a n substituted 2 nitrobenzylamine is heated in the presence of base such as naoh and koh and an alcohol and includes the formation of a carbanion 3 the reaction begins with the base removing a hydrogen 1 adjacent to the secondary amine group creating a carbanion the carbanion then extracts an oxygen from the nitro group 2 which is then subsequently protonated most likely by water the newly formed hydroxyl group 3 then extracts the secondary amines hydrogen leaving a negative charge on nitrogen and creating a protonated hydroxyl group the oxygen and its hydrogens then leave as a molecule of water 4 creating a double bond with the previously negatively charged nitrogen atom the new pi bond makes the carbon adjacent to the nitrogen more susceptible for attack by a present alcohol 5 which in turn creates an oxygen carbon bond a bond between the two nitrogen atoms and pushes electrons onto the oxygen molecule originally from the amide this molecule is then protonated 6 to create an overall net neutral charge the hydroxyl group is protonated similarly to step three 7 creating a good leaving group therefore when the alpha hydrogen of the nitrogen atom and ether group 8 is extracted by the base the flow of electrons creates two new carbon nitrogen bonds and causes the loss of the protonated hydroxyl group as a molecule of water the final product produced by this mechanism is therefore a 3 oxy substituted 2 h indazole slight variations of this mechanism exists depending on the starting materials and the conditions acid or base of the reaction 2 1 in instances of intramolecular oxygen attack i e step 5 of the proposed mechanism is intramolecular an o nitrobenzylidene imine intermediate is formed compared to the secondary imine of the displayed mechanism 2 o nitrosobenzylidine imine furthermore davis beirut reactions in acids form a carbocation as one of its transition states instead of the proposed carbanion one when the reaction occurs in base 3 other variants of the davis beirut reaction edit by manipulating the starting materials of the davis beirut reaction researchers can create a large number of 2 h indazoles derivatives many of which can be utilized for further synthesis 1 6 in 2014 thiazolo thiazino and thiazipino 2 h indazoles were synthesized utilizing o nitrobenzaldehydes or o nitrobenzyl bromides and s trityl protected primary aminothiol alkanes with a base such as koh in alcohol 1 creating thiazolo thiazino and thiazipino 2 h indazoles is beneficial since they are generally more stable than the oxo 2 h indazoles formed without the s trityl protected group and they can easily be oxidized to sulfones 1 1 h indazole example creating 2 h indazoles via the davis beirut reaction can also help in producing 1 h indazoles naturally occurring and synthetically made molecules with known pharmaceutical uses such as anti inflammatories and anti cancer drugs 6 8 by creating 2 h indazoles via the davis beirut reaction the product can subsequently be reacted with electrophiles such as anhydrides to create disubstituted 1 h indazoles that can be utilized for pharmaceutical and other industrial purposes 6 applications edit heterocycles especially those containing nitrogen atoms are highly prevalent in many pharmaceutical drugs currently on the market 4 some like those coming from 1 h indazoles contain naturally occurring molecules while others are purly synthetic 8 2 h indazoles though are very rare in nature compared to 1 h indazole compounds most likely due to the complex nature of a heterocycle including a nitrogen nitrogen bond and an ether side chain 9 the discovery of the davis beirut reaction therefore provides any easy and cost effective way to synthetically create 2 h indazoles 4 breakthroughs including the success of introducing thioether moiety at c3 of the 2 h indazole structure has aided in creating drug treatments for a variety of ailments including cystic fibrosis with the use of myeloperoxidase inhibitors 4 6 10 due to the recentness of the discovery of this reaction though most research is primarily headed by haddadin kurth or both therefore causing a currently limited scope 3 references edit 1 2 3 4 5 farber kelli haddadin makhluf kurth mark 2014 davis beirut reaction route to thiazolo thizaino and thiazepino 2h indazoles the journal of organic chemistry 79 15 6939 6945 doi 10 1021 jo501014e pmc 4120971 pmid 25019525 1 2 3 avila belem el dakdouki mohammad nazer musa harrison jason haddadin makhluf kurth mark november 28 2012 acid and base catalyzed davis beirut reaction experimental and theoretical mechanistic studies and synthesis of novel 3 amino 2h indazoles tetrahedron letters 53 48 6475 6478 doi 10 1016 j tetlet 2012 09 026 pmc 3489190 pmid 23139435 1 2 3 4 5 kurth mark j olmstead marilyn m haddadin makhluf j 2005 claimed 2 1 benzisoxazoles are indazalones the journal of organic chemistry 70 3 1060 1062 doi 10 1021 jo048153i issn 0022 3263 pmid 15675871 1 2 3 4 mills aaron d nazer musa z haddadin makhluf j kurth mark j 2006 n n bond forming heterocyclization synthesis of 3 alkoxy 2h indazoles the journal of organic chemistry 71 7 2687 2689 doi 10 1021 jo0524831 issn 0022 3263 pmid 16555821 zhu jie s haddadin makhluf j kurth mark j 22 july 2019 davis beirut reaction diverse chemistries of highly reactive nitroso intermediates in heterocycle synthesis accounts of chemical research 52 8 2256 2265 doi 10 1021 acs accounts 9b00220 pmc 6702092 pmid 31328502 1 2 3 4 5 conrad wayne e fukazawa ryo haddadin makhluf j kurth mark j 2011 the davis beirut reaction n1 n2 disubstituted 1h indazolones via 1 6 electrophilic addition to 3 alkoxy 2h indazoles organic letters 13 12 3138 41 doi 10 1021 ol2010424 pmc 3112251 pmid 21612219 davis beirut reaction town recognizes gown and vice versa 30 aug 2013 1 2 bermudez jose fake charles s joiner graham f joiner karen a king frank d miner wesley d sanger gareth j july 1990 5 hydroxytryptamine 5 ht3 receptor antagonists 1 indazole and indolizine 3 carboxylic acid derivatives journal of medicinal chemistry 33 7 1924 1929 doi 10 1021 jm00169a016 issn 0022 2623 pmid 2362270 el dakdouki mohammad h hussein abdulsattar abdallah hiba shatila rania mouneimne youssef september 2017 synthesis of novel 2 h indazole analogues via the davis beirut reaction and conjugation onto magnetic nanoparticles tetrahedron 73 39 5769 5777 doi 10 1016 j tet 2017 08 027 issn 0040 4020 prof haddadin on the davis beirut reaction university of balamand november 19 2017 archived from the original on may 8 2018 retrieved may 7 2018 retrieved from https en wikipedia org w index php title davis beirut_reaction oldid 1323658415 categories indazoles nitrogen heterocycle forming reactions name reactions hidden categories articles with short description short description matches wikidata this page was last edited on 23 november 2025 at 01 59 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 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