The Staudinger reduction is conducted in two steps. - 22.214.171.124. RSC Adv 4:5660–5665. Chem Rev 105:559–592. Fifteen azides with different functional groups were well reduced to the corresponding amines in excellent yields. Summary.  The reaction follows this stoichiometry: The Staudinger reduction is conducted in two steps. Cryst Growth Des 13:1050–1058. The full text of this article hosted at iucr.org is unavailable due to technical difficulties. doi:10.1039/C3RA46594B, Thordarson P (2011) Determining association constants from titration experiments in supramolecular chemistry. doi:10.1016/j.bmcl.2005.06.074, Shen LL, Mitscher LA, Sharma PN, O’Donnell TJ, Chu DTW, Cooper CS, Rosen T, Pernet AG (1989) Mechanism of inhibition of DNA gyrase by quinolone antibacterials: a cooperative drug-DNA binding model. and you may need to create a new Wiley Online Library account. The Mechanism of Amide Reduction by LiAlH 4 Primary and secondary amides have a proton connected to the nitrogen that is acidic enough to be attacked by the hydride. doi:10.1007/s00894-007-0233-4, Tapia-Juárez M, González-Campos JB, Contreras-Celedón C, Corona D, Cuevas-Yañez E, Chacón-García L (2014) A new type of anion receptor: pyrrolyl quinones. Phosphinmethylenderivate und Phosphinimine", Staudinger Reaction at organic-chemistry.org, https://en.wikipedia.org/w/index.php?title=Staudinger_reaction&oldid=977897474, Creative Commons Attribution-ShareAlike License, This page was last edited on 11 September 2020, at 16:57. J Biol Chem 273:27668–27677. Amides, RCONR' 2, can be reduced to the amine, RCH 2 NR' 2 by conversion of the C=O to -CH 2- Amides can be reduced by LiAlH 4 but NOT the less reactive NaBH 4 An efficient reduction of azide to amine: a new methodology to synthesize ethyl 7-amino-1-ethyl-6,8-difluoroquinolone-3-carboxylate and its spectroscopic characterization. A theoretical study. 71, 939–947 (2017). © 2020 Springer Nature Switzerland AG. doi:10.1039/C0CS00062K, Vega-Rodríguez S, Jiménez-Cataño R, Leyva E, Loredo-Carrillo SE (2013) Intramolecular hydrogen bonds in fluorinated, methoxylated, or unsubstituted 2-(anilino)-1,4-naphthoquinones. The intermediate, e.g. J Am Chem Soc 134:71–74. doi:10.1007/BF00769385, Hartwing JF, Shekhar S, Shen Q, Barrios-Landeros F (2007) The chemistry of anilines. doi:10.1021/ct100408b, Kovács A, Szabó A, Hargittai I (2002) Structural characteristics of intramolecular hydrogen bonding in benzene derivatives. Triphenylphosphine or tributylphosphine are most commonly used, yielding tributylphosphine oxide or triphenylphosphine oxide as a side product in addition to the desired amine. Acc Chem Res 35:887–894. 6H 2 O or Fe/BiCl 3 system in H 2 O/ethanol (2:1, V:V) at room temperature.Fifteen azides with different functional groups were well reduced to the corresponding amines in excellent yields. Chem. The reaction mechanism centers around the formation of an iminophosphorane through nucleophilic addition of the aryl or alkyl phosphine at the terminal nitrogen atom of the organic azide and expulsion of diatomic nitrogen. doi:10.1016/j.tetlet.2008.07.156, Mafra L, Santos SM, Siegel R, Alves I, Almeida-Paz FA, Dudenko D, Spiess HW (2012) Packing interactions in hydrated and anhydrous forms of the antibiotic ciprofloxacin: a solid-state NMR, X-ray diffraction, and computer simulation study. Zeitschrift für Naturforschung B 62:1045–1051. Unlimited viewing of the article PDF and any associated supplements and figures. Pharm Chem J 24:43–47. , In one application this reaction is used to create a bond between a nucleoside and a fluorescent marker:, The Staudinger ligation is used to site-specifically incorporate organic molecules (such as fluorescent dyes) into recombinant polypeptides containing unnatural azide-conjugated aminoacids (incorporated, for instance, via suppression of the amber stop codon: https://pubs.acs.org/doi/pdf/10.1021/ja027007w), For the reaction between imines and ketenes to form, https://pubs.acs.org/doi/pdf/10.1021/ja027007w, "Über neue organische Phosphorverbindungen III. doi:10.1021/ja025896h, Soni K (2012) Fluoroquinolones: chemistry & action. Tetrahedron Lett 49:6759–6761. First phosphine imine-forming reaction is conducted involving treatment of the azide with the phosphine. Part of Springer Nature. Indo Global J Pharm Sci 2:43–53. Unlimited viewing of the article/chapter PDF and any associated supplements and figures. Enter your email address below and we will send you your username, If the address matches an existing account you will receive an email with instructions to retrieve your username, I have read and accept the Wiley Online Library Terms and Conditions of Use.
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