A green, practical & scalable approach towards the synthesis of valuable α-keto amides using a metal-free catalyst under solvent-free conditions
α-Ketoamides are very important motifs as they are present in many natural products, drugs & biologically important molecules. We synthesized a very simple, cheap, eco-friendly & reusable glucose-based carbonaceous material (GCM), which showed high performance as a catalyst in the oxidative...
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Veröffentlicht in: | New journal of chemistry 2023-10, Vol.47 (42), p.19679-19687 |
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container_issue | 42 |
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container_title | New journal of chemistry |
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creator | Bankar, Shubham R Ghadge, Sambhaji S Jadhav, Vrushali H |
description | α-Ketoamides are very important motifs as they are present in many natural products, drugs & biologically important molecules. We synthesized a very simple, cheap, eco-friendly & reusable glucose-based carbonaceous material (GCM), which showed high performance as a catalyst in the oxidative cross-dehydrogenative coupling (CDC) reaction of α-ketoaldehydes with amines for the synthesis of α-ketoamides. The GCM catalyst was also very efficient for one-pot two-step synthesis of α-ketoamides from α-ketoalcohols as well. The GCM catalyst was able to catalyze alcohol oxidation in α-ketoalcohols followed by CDC reaction with amines to form α-ketoalcohols. The reactions were found to proceed smoothly at a low temperature of 50 °C using a green & economical metal-free catalyst under base-free, ligand-free & solvent-free reaction conditions to get the corresponding α-ketoamides in good to excellent yields. The results demonstrated that the GCM catalyst showed acidic as well as superior oxidising catalytic activity due to the presence of a carboxylic acid (-COOH) and hydroxyl (-OH)-enriched carbonaceous framework, which enabled the synthesis of important α-ketoamide motifs. The applicability of the catalyst was also evaluated for the synthesis of an anti-HIV agent drug molecule.
Greener, cheaper & eco-friendly GCM catalyst as well as catalytic process for synthesis of α-Keto Amides. |
doi_str_mv | 10.1039/d3nj03087c |
format | Article |
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Greener, cheaper & eco-friendly GCM catalyst as well as catalytic process for synthesis of α-Keto Amides.</description><identifier>ISSN: 1144-0546</identifier><identifier>EISSN: 1369-9261</identifier><identifier>DOI: 10.1039/d3nj03087c</identifier><language>eng</language><publisher>Cambridge: Royal Society of Chemistry</publisher><subject>Acidic oxides ; Amides ; Amines ; Carbonaceous materials ; Carboxylic acids ; Catalysts ; Catalytic activity ; Chemical synthesis ; Dehydrogenation ; Low temperature ; Natural products ; Oxidation ; Solvents</subject><ispartof>New journal of chemistry, 2023-10, Vol.47 (42), p.19679-19687</ispartof><rights>Copyright Royal Society of Chemistry 2023</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-c240t-5be8608a36742723c0eb614f900b8f979c785bb1e6302677cd5a229a0a84b46f3</cites><orcidid>0000-0002-4678-4045</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27901,27902</link.rule.ids></links><search><creatorcontrib>Bankar, Shubham R</creatorcontrib><creatorcontrib>Ghadge, Sambhaji S</creatorcontrib><creatorcontrib>Jadhav, Vrushali H</creatorcontrib><title>A green, practical & scalable approach towards the synthesis of valuable α-keto amides using a metal-free catalyst under solvent-free conditions</title><title>New journal of chemistry</title><description>α-Ketoamides are very important motifs as they are present in many natural products, drugs & biologically important molecules. We synthesized a very simple, cheap, eco-friendly & reusable glucose-based carbonaceous material (GCM), which showed high performance as a catalyst in the oxidative cross-dehydrogenative coupling (CDC) reaction of α-ketoaldehydes with amines for the synthesis of α-ketoamides. The GCM catalyst was also very efficient for one-pot two-step synthesis of α-ketoamides from α-ketoalcohols as well. The GCM catalyst was able to catalyze alcohol oxidation in α-ketoalcohols followed by CDC reaction with amines to form α-ketoalcohols. The reactions were found to proceed smoothly at a low temperature of 50 °C using a green & economical metal-free catalyst under base-free, ligand-free & solvent-free reaction conditions to get the corresponding α-ketoamides in good to excellent yields. The results demonstrated that the GCM catalyst showed acidic as well as superior oxidising catalytic activity due to the presence of a carboxylic acid (-COOH) and hydroxyl (-OH)-enriched carbonaceous framework, which enabled the synthesis of important α-ketoamide motifs. The applicability of the catalyst was also evaluated for the synthesis of an anti-HIV agent drug molecule.
Greener, cheaper & eco-friendly GCM catalyst as well as catalytic process for synthesis of α-Keto Amides.</description><subject>Acidic oxides</subject><subject>Amides</subject><subject>Amines</subject><subject>Carbonaceous materials</subject><subject>Carboxylic acids</subject><subject>Catalysts</subject><subject>Catalytic activity</subject><subject>Chemical synthesis</subject><subject>Dehydrogenation</subject><subject>Low temperature</subject><subject>Natural products</subject><subject>Oxidation</subject><subject>Solvents</subject><issn>1144-0546</issn><issn>1369-9261</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><recordid>eNpFkctO3EAQRS1EJB5hkz1SSUgsIhz65ba9HE1CHkJhQ9ZWud1mPHi6TVebaD4jn5If4ZvoMIis7pXq6F5VVZZ94OwTZ7K-7KRbM8mq0uxlh1zqOq-F5vvJc6VyVih9kB0RrRnjvNT8MPuzgLtgrbuAKaCJg8ERzoGSYDtawGkKHs0Kov-NoSOIKwu0dUloIPA9POI4v6BPf_N7Gz3gZugswUyDuwOEjY045n3qAIPJbinC7DobgPz4aF18nXnXDXHwjt5n73ocyZ686nH26-rL7fJbfn3z9ftycZ0boVjMi9ZWmlUodalEKaRhttVc9TVjbdXXZW3KqmhbbrVkQpel6QoUokaGlWqV7uVxdrbLTRs-zJZis_ZzcKmyEVUlixSkeKI-7igTPFGwfTOFYYNh23DW_Dt581n-_PFy8mWCT3dwIPPG_X-JfAbpmX-0</recordid><startdate>20231030</startdate><enddate>20231030</enddate><creator>Bankar, Shubham R</creator><creator>Ghadge, Sambhaji S</creator><creator>Jadhav, Vrushali H</creator><general>Royal Society of Chemistry</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>H9R</scope><scope>JG9</scope><scope>KA0</scope><orcidid>https://orcid.org/0000-0002-4678-4045</orcidid></search><sort><creationdate>20231030</creationdate><title>A green, practical & scalable approach towards the synthesis of valuable α-keto amides using a metal-free catalyst under solvent-free conditions</title><author>Bankar, Shubham R ; Ghadge, Sambhaji S ; Jadhav, Vrushali H</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c240t-5be8608a36742723c0eb614f900b8f979c785bb1e6302677cd5a229a0a84b46f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><topic>Acidic oxides</topic><topic>Amides</topic><topic>Amines</topic><topic>Carbonaceous materials</topic><topic>Carboxylic acids</topic><topic>Catalysts</topic><topic>Catalytic activity</topic><topic>Chemical synthesis</topic><topic>Dehydrogenation</topic><topic>Low temperature</topic><topic>Natural products</topic><topic>Oxidation</topic><topic>Solvents</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Bankar, Shubham R</creatorcontrib><creatorcontrib>Ghadge, Sambhaji S</creatorcontrib><creatorcontrib>Jadhav, Vrushali H</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Illustrata: Natural Sciences</collection><collection>Materials Research Database</collection><collection>ProQuest Illustrata: Technology Collection</collection><jtitle>New journal of chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Bankar, Shubham R</au><au>Ghadge, Sambhaji S</au><au>Jadhav, Vrushali H</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A green, practical & scalable approach towards the synthesis of valuable α-keto amides using a metal-free catalyst under solvent-free conditions</atitle><jtitle>New journal of chemistry</jtitle><date>2023-10-30</date><risdate>2023</risdate><volume>47</volume><issue>42</issue><spage>19679</spage><epage>19687</epage><pages>19679-19687</pages><issn>1144-0546</issn><eissn>1369-9261</eissn><abstract>α-Ketoamides are very important motifs as they are present in many natural products, drugs & biologically important molecules. We synthesized a very simple, cheap, eco-friendly & reusable glucose-based carbonaceous material (GCM), which showed high performance as a catalyst in the oxidative cross-dehydrogenative coupling (CDC) reaction of α-ketoaldehydes with amines for the synthesis of α-ketoamides. The GCM catalyst was also very efficient for one-pot two-step synthesis of α-ketoamides from α-ketoalcohols as well. The GCM catalyst was able to catalyze alcohol oxidation in α-ketoalcohols followed by CDC reaction with amines to form α-ketoalcohols. The reactions were found to proceed smoothly at a low temperature of 50 °C using a green & economical metal-free catalyst under base-free, ligand-free & solvent-free reaction conditions to get the corresponding α-ketoamides in good to excellent yields. The results demonstrated that the GCM catalyst showed acidic as well as superior oxidising catalytic activity due to the presence of a carboxylic acid (-COOH) and hydroxyl (-OH)-enriched carbonaceous framework, which enabled the synthesis of important α-ketoamide motifs. The applicability of the catalyst was also evaluated for the synthesis of an anti-HIV agent drug molecule.
Greener, cheaper & eco-friendly GCM catalyst as well as catalytic process for synthesis of α-Keto Amides.</abstract><cop>Cambridge</cop><pub>Royal Society of Chemistry</pub><doi>10.1039/d3nj03087c</doi><tpages>9</tpages><orcidid>https://orcid.org/0000-0002-4678-4045</orcidid></addata></record> |
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source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
subjects | Acidic oxides Amides Amines Carbonaceous materials Carboxylic acids Catalysts Catalytic activity Chemical synthesis Dehydrogenation Low temperature Natural products Oxidation Solvents |
title | A green, practical & scalable approach towards the synthesis of valuable α-keto amides using a metal-free catalyst under solvent-free conditions |
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