{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,5,5]],"date-time":"2026-05-05T10:08:14Z","timestamp":1777975694968,"version":"3.51.4"},"reference-count":19,"publisher":"MDPI AG","issue":"20","license":[{"start":{"date-parts":[[2020,10,17]],"date-time":"2020-10-17T00:00:00Z","timestamp":1602892800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100006769","name":"Russian Science Foundation","doi-asserted-by":"publisher","award":["20-43-05002"],"award-info":[{"award-number":["20-43-05002"]}],"id":[{"id":"10.13039\/501100006769","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Aminomethylhydroxymethylfuran derivatives are well known compounds which are used in the pharmaceutical industry. Reductive amination of 5-hydroxymethylfurfural (HMF) derived from available non-edible lignocellulosic biomass is an attractive method for the synthesis of this class of compounds. In the present study, the synthesis of N-substituted 5-(hydroxymethyl)-2-furfuryl amines and 5-(acetoxymethyl)-2-furfuryl amines was performed by two-step process, which includes the condensation of furanic aldehydes (HMF and 5-acetoxymethylfurfural) with primary amines in methanol on the first step and the reduction of obtained imines with hydrogen in a flow reactor over CuAlOx catalyst derived from layered double hydroxide on the second step. This process does not require isolation and purification of intermediate imines and can be used to synthesize a number of aminomethylhydroxymethylfurans in good to excellent yield.<\/jats:p>","DOI":"10.3390\/molecules25204771","type":"journal-article","created":{"date-parts":[[2020,10,17]],"date-time":"2020-10-17T08:14:50Z","timestamp":1602922490000},"page":"4771","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":24,"title":["Two-Step One-Pot Reductive Amination of Furanic Aldehydes Using CuAlOx Catalyst in a Flow Reactor"],"prefix":"10.3390","volume":"25","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-1111-4524","authenticated-orcid":false,"given":"Alexey L.","family":"Nuzhdin","sequence":"first","affiliation":[{"name":"Boreskov Institute of Catalysis SB RAS, 630090 Novosibirsk, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Marina V.","family":"Bukhtiyarova","sequence":"additional","affiliation":[{"name":"Boreskov Institute of Catalysis SB RAS, 630090 Novosibirsk, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Valerii I.","family":"Bukhtiyarov","sequence":"additional","affiliation":[{"name":"Boreskov Institute of Catalysis SB RAS, 630090 Novosibirsk, Russia"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2020,10,17]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"4278","DOI":"10.1021\/jm00051a004","article-title":"Cholinergic Agents Structurally Related to Furtrethonium. 2. Synthesis and Antimuscarinic Activity of a Series of N-[5-[(1\u2032-Substituted-acetoxy)methyl]-2-furfuryl]dialkylamines","volume":"37","author":"Feriani","year":"1994","journal-title":"J. Med. Chem."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"2494","DOI":"10.1039\/C8GC00915E","article-title":"One-pot synthesis of amines from biomass resources catalyzed by HReO4","volume":"20","author":"Caetano","year":"2018","journal-title":"Green Chem."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"3880","DOI":"10.1039\/C7GC01579H","article-title":"Versatile CO-assisted direct reductive amination of 5-hydroxymethylfurfural catalyzed by a supported gold catalyst","volume":"19","author":"Zhu","year":"2017","journal-title":"Green Chem."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"184","DOI":"10.1016\/j.indcrop.2018.12.082","article-title":"Production of 5-hydroxymethylfurfural and levulinic acid from lignocellulosic biomass and catalytic upgradation","volume":"130","author":"Li","year":"2019","journal-title":"Ind. Crop. Prod."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"230","DOI":"10.1016\/j.rser.2017.02.042","article-title":"Recent advances in catalytic transformation of biomass-derived 5-hydroxymethylfurfural into the innovative fuels and chemicals","volume":"74","author":"Hu","year":"2017","journal-title":"Renew. Sustain. Energy Rev."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"14181","DOI":"10.1021\/acs.chemrev.6b00486","article-title":"Biobased Amines: From Synthesis to Polymers; Present and Future","volume":"116","author":"Froidevaux","year":"2016","journal-title":"Chem. Rev."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"59083","DOI":"10.1039\/C4RA10349A","article-title":"Direct reductive amination of 5-hydroxymethylfurfural with primary\/secondary amines via Ru-complex catalyzed hydrogenation","volume":"4","author":"Xu","year":"2014","journal-title":"RSC Adv."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"6243","DOI":"10.1021\/acssuschemeng.8b06631","article-title":"Chemicals from Biomass: Selective Synthesis of N-Substituted Furfuryl Amines by the One-Pot Direct Reductive Amination of Furanic Aldehydes","volume":"7","author":"Vidal","year":"2019","journal-title":"ACS Sustain. Chem. Eng."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"368","DOI":"10.1039\/C9GC03140E","article-title":"Efficient reductive amination of HMF with well dispersed Pd nanoparticles immobilized in a porous MOF\/polymer composite","volume":"22","author":"Karve","year":"2020","journal-title":"Green Chem."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"1201","DOI":"10.1039\/c002340j","article-title":"Production of biobased HMF derivatives by reductive amination","volume":"12","author":"Cukalovic","year":"2010","journal-title":"Green Chem."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"3590","DOI":"10.1002\/cssc.201500804","article-title":"Continuous Reductive Amination of Biomass-Derived Molecules over Carbonized Filter Paper-Supported FeNi Alloy","volume":"8","author":"Chieffi","year":"2015","journal-title":"ChemSusChem"},{"key":"ref_12","doi-asserted-by":"crossref","unstructured":"Nuzhdin, A.L., Bukhtiyarova, M.V., and Bukhtiyarova, G.A. (2020). Cu-Al mixed oxide derived from layered double hydroxide as an efficient catalyst for continuous-flow reductive amination of aromatic aldehydes. J. Chem. Technol. Biotechnol.","DOI":"10.1002\/jctb.6508"},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"56743","DOI":"10.1039\/C4RA09605C","article-title":"Expanding the utility of flow hydrogenation\u2014A robust protocol restricting hydrodehalogenation","volume":"4","author":"Hizartzidis","year":"2014","journal-title":"RSC Adv."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"111132","DOI":"10.1016\/j.mcat.2020.111132","article-title":"Flow hydrogenation of 5-acetoxymethylfurfural over Cu-based catalysts","volume":"494","author":"Nuzhdin","year":"2020","journal-title":"Mol. Catal."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"2266","DOI":"10.1002\/cssc.201402095","article-title":"Tunable and Selective Conversion of 5-HMF to 2,5-Furandimethanol and 2,5-Dimethylfuran over Copper-Doped Porous Metal Oxides","volume":"7","author":"Kumalaputri","year":"2014","journal-title":"ChemSusChem"},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"489","DOI":"10.1021\/cr60225a003","article-title":"The Chemistry of Imines","volume":"63","author":"Layer","year":"1963","journal-title":"Chem. Rev."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"1179","DOI":"10.1002\/cssc.201403252","article-title":"From Lignocellulosic Biomass to Furans via 5-Acetoxymethylfurfural as an Alternative to 5-Hydroxymethylfurfural","volume":"8","author":"Kang","year":"2015","journal-title":"ChemSusChem"},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"2496","DOI":"10.1039\/C7GC00975E","article-title":"Cellulose acetate as a convenient intermediate for the preparation of 5-acetoxymethylfurfural from biomass","volume":"19","author":"Esposito","year":"2017","journal-title":"Green Chem."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"8770","DOI":"10.1002\/slct.201802040","article-title":"Cascade Synthesis of 5-(Acetoxymethyl)furfural from Carbohydrates over Sn-Mont Catalyst","volume":"3","author":"Shinde","year":"2018","journal-title":"ChemistrySelect"}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/25\/20\/4771\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T10:23:03Z","timestamp":1760178183000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/25\/20\/4771"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2020,10,17]]},"references-count":19,"journal-issue":{"issue":"20","published-online":{"date-parts":[[2020,10]]}},"alternative-id":["molecules25204771"],"URL":"https:\/\/doi.org\/10.3390\/molecules25204771","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2020,10,17]]}}}