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 doi:10.1074/jbc.273.42.27668, Korth M (2010) Third-generation hydrogen-bonding corrections for semiempirical QM methods and force fields. An expeditious synthesis of novel fluoroquinolone derivatives. 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. We wish to thank CONACYT (SEP-82585) and UASLP (C11-FRC-09-37.7) for their financial support. Staudinger reduction. and you may need to create a new Wiley Online Library account. 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. doi:10.3987/COM-98-8143, Khodursky AB, Cozzarelli NR (1998) The mechanism of inhibition of topoisomerase IV by quinolone antibacterials. triphenylphosphine phenylimide, is then subjected to hydrolysis to produce a phosphine oxide and an amine: The overall conversion is a mild method of reducing an azide to an amine. 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.  In aqueous media, the aza-ylide intermediate rearranges, to produce an amide linkage and the phosphine oxide, and is so named the Staudinger ligation because it ligates two molecules together, whereas in the classical Staudinger reaction, the two products are not covalently linked after hydrolysis. We have found that the yields of the amine obtained by catalytic hydrogenation are, in some cases, low or variable, and the products are difficult to purify'. doi:10.1039/C3RA46594B, Thordarson P (2011) Determining association constants from titration experiments in supramolecular chemistry. Triphenylphosphine or tributylphosphine are most commonly used, yielding tributylphosphine oxide or triphenylphosphine oxide as a side product in addition to the desired amine. The intermediate, e.g. J Biol Chem 273:27668–27677. J Am Chem Soc 124:10887–10893. Manuel Nava 6, Zona Universitaria, San Luis Potosí, SLP, 78210, Mexico, Socorro Leyva-Ramos, Rogelio Jiménez-Cataño & Sarai Vega-Rodríguez, Unidad Académica de Ciencias Químicas, Universidad Autónoma de Zacatecas, Carretera Zacatecas-Guadalajara Km 6, Ejido la Escondida s/n, Edificio 6, Zacatecas, Zac, 98136, Mexico, Instituto de Investigaciones Químico Biológicas, Universidad Michoacana de San Nicolás de Hidalgo, Edificio B-1, Ciudad Universitaria, Morelia, Mich, 58066, Mexico, You can also search for this author in The full text of this article hosted at iucr.org is unavailable due to technical difficulties. doi:10.1021/ja00082a011, Glushkov RG, Dronova LN, Elina AS, Porokhovaya MV, Padeiskaya EN, Radkevich TP, Shipilnova LD (1990) Synthesis and biological examination of tricyclic analogs of oxolinic acid. https://doi.org/10.1007/s11696-016-0016-4. doi:10.1021/ct100408b, Kovács A, Szabó A, Hargittai I (2002) Structural characteristics of intramolecular hydrogen bonding in benzene derivatives. doi:10.1016/j.bmcl.2003.10.059, Zhen P-W, Xie X-M, Wang W, Wang X-J, Guo Y-P, Tu Q-D (2006) Reduction of azide to amine using Fe/AlCl3 or Fe/BiCl3 system in aqueous EtOH.
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