Selective Reduction of Aromatic Azides with Hexamethyldisilathiane: Synthesis of New 2-Azidopyrrolo[2,1-c][1,4]benzodiazepines. Herein, we show that heterogeneous nanoparticle catalysts enable site-selective monoreduction of polyazide substrates for the generation of aminoglycoside antibiotic derivatives. Find more information on the Altmetric Attention Score and how the score is calculated. You’ve supercharged your research process with ACS and Mendeley! chemoselectivity in high yields. Experimental 2.1 Preparation and Characterization Electroplating experiment was performed using a constant potential mode with gold wire ûФ100 μm, signed as Au) as working electrode, silver wire and Smritilekha Bera, Dhananjoy Mondal, Jacob T. Martin, Man Singh. the Altmetric Attention Score and how the score is calculated. transformations in water. Article Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. Yuecheng Zhang, Xulin Han, Jiquan Zhao, Zijian Qian, Tianmei Li, Yuqing Tang, Hong‐Yu Zhang. Sodium Amalgam, a Useful Reducing Reagent for Formation of Amines from Azides Bearing a Variety of Functional Groups. In summary, Pd/C-catalyzed transfer hydrogenation with Hantzsch 1,4-dihydropyridine was found to be very effective for the selective reduction of aromatic azides to the corresponding amines. Rh/Al2O3 can be used as an effective chemo-selective reductive catalyst that combines the mild conditions of catalytic hydrogenation with high selectivity for azide moieties in the presence of other hydrogenolysis labile groups such as benzyl and benzyloxycarbonyl functionalities. Mo(CO)6 Mediated Selective Reduction of Azides and Nitro Compounds to Amines Under Neutral Conditions. For permission to reproduce, republish and Learn more. Save any article or search result from DeepDyve, PubMed, and Google Scholar... all in one place. Stereoselective Synthesis of α- and β-Glycofuranosyl Amides by Traceless Ligation of Glycofuranosyl Azides. jo0266947si20030413_082604.pdf (329.18 kb), http://pubs.acs.org/page/copyright/permissions.html, https://doi.org/10.1016/B978-0-12-817467-8.00001-3, https://doi.org/10.1016/j.tetlet.2018.07.066, https://doi.org/10.1016/j.carres.2015.02.008, https://doi.org/10.1016/B978-0-08-097742-3.00816-8, https://doi.org/10.1016/j.tetlet.2013.07.110, https://doi.org/10.1007/s11172-011-0195-7, https://doi.org/10.1002/9780471264194.fos00902.pub2, https://doi.org/10.1016/j.cclet.2008.05.031, https://doi.org/10.1016/j.tetasy.2008.03.018, https://doi.org/10.1016/j.tetasy.2006.08.021, https://doi.org/10.1016/j.bmc.2005.08.004, https://doi.org/10.1016/j.tetlet.2004.06.112. Please check your email for instructions on resetting your password. Working off-campus? in situ Herein, we show that heterogeneous nanoparticle catalysts enable site-selective monoreduction of polyazide substrates for the generation of aminoglycoside antibiotic derivatives. Copyright © 2020 Elsevier B.V. or its licensors or contributors. Require these words, in this exact order. H. Sajiki, Tetrahedron Lett., 1995, 36, 3465-3468. Kesavan Manibalan, Veerappan Mani, Pu-Chieh Chang, Chih-Hung Huang, Sheng-Tung Huang, Kasper Marchlewicz, Suresh Neethirajan. methodology has been applied towards the preparation of biologically important ChemInform Site-selective modification of bioactive natural products is an effective approach to generating new leads for drug discovery. Electronic Supporting Information files are available without a subscription to ACS Web Editions. By continuing you agree to the use of cookies. A broad functional‐group compatibility, chemoselective reduction of aldehydes in the presence of ketones, and selective reduction of isatins at the C3 carbonyl group are the highlights of the present method. Download : Download high-res image (90KB)Download : Download full-size image. Unlimited access to over18 million full-text articles. by employing borontrifluoride diethyl etherate and sodium iodide. Patricia Y. Hayes, Benjamin P. Ross, Bradley G. Thomas, Istvan Toth. Selective synthesis of mono- and di-methylated amines using methanol and sodium azide as C1 and N1 sources. 1297-1300. Get article recommendations from ACS based on references in your Mendeley library. A novel enantioselective synthesis of α-amino acids has been developed, Suitable nitrogen nucleophiles include phthalimide or hydrogen azide; subsequent hydrolysis (in the case of using phthalimide, see Gabriel Synthesis) or selective reduction (in the case of azide formation, see Staudinger Reaction) makes the corresponding amines accessible. superior solvent over ionic liquids by severalfold in promoting the I. Bosch, A. M. Costa, M. Martín, F. Urpí, J. Vilarrasa,
A synthesis of (+)-estrone relies on selective hydrosilane reduction of a conjugated alkene as a key step. Chem. The aldehyde and keto groups are selectively reduced in the presence of azide, cyano, epoxy, ester, and carbon–carbon double‐bond functional groups. Synthesis and characteristics of sugar-phosphoramidates: A spectroscopic study. Lewis Base Catalyzed Intramolecular Reduction of Salicylaldehydes by Pinacol‐Derived Chlorohydrosilane. with dichloroindium hydride under very mild conditions. Information about how to use the RightsLink permission system can be found at Catalytic Asymmetric Huisgen Alkyne-Azide Cycloaddition of Bisalkynes by Copper(I) Nanoparticles. Find more information about Crossref citation counts. Sridhar, Perali Ramu; Prabhu, Kandikere Ramaiah; Chandrasekaran, Srinivasan. The surface hydrogen on copper nanoparticles is from the ACS website, either in whole or in part, in either machine-readable form or any other form Search Find more information about Crossref citation counts. B. Gopal Reddy,, K. P. Madhusudanan, and. The practicality of this strategy is exemplified with a range of azide-containing carbohydrate and amino acid derivatives. Synthesis of β‐Trifluoromethylated Alkyl Azides
Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. DeepDyve's default query mode: search by keyword or DOI. (2004). Studies on reactivity of azidoamides, intermediates in the synthesis of tetrahydroxypipecolic acid derivatives. intramolecular reductive-cyclization process. Site-Selective Conversion of Azido Groups at Carbonyl α-Positions to Diazo Groups in Diazido and Triazido Compounds. SnCl4/Sn catalyzed chemoselective reduction of glycopyranosyl azides for the synthesis of diversely functionalized glycopyranosyl chloroacetamides. S. Reddy, Synlett, 2008, Published by Elsevier Ltd. https://doi.org/10.1016/j.carres.2020.107948. the Altmetric Attention Score and how the score is calculated. 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, orcid.org/http://orcid.org/0000-0003-4130-2841, I have read and accept the Wiley Online Library Terms and Conditions of Use. We hypothesize that the observed selectivity is derived from the greater ability of less-hindered azide groups to interact with the surface of the nanoparticle catalyst. Afraz Subratti, Lorale J. Lalgee, Nigel Kevin Jalsa. Aryl azides undergo clean reduction by copper nanoparticles in water in the A. Postigo, S. Kopsov, C. Ferreri, C. Chatgilialoglu, Org. 7H2O/NaI System. Thanks for helping us catch any problems with articles on DeepDyve. A selective and facile method allows the reduction of aromatic azides to amines We'll do our best to fix them. High regioselectivity for monoazide reduction is shown to favor reduction of the least sterically hindered azide. http://pubs.acs.org/page/copyright/permissions.html. of interest in chemistry, biology, medicine. The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acscatal.6b01217. hydrogenation of various functional groups using
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