Synthesis of Nitroaromatic Compounds via Three-Component Ring Transformations
1-Methyl-3,5-dinitro-2-pyridone serves as an excellent substrate for nucleophilic-type ring transformation because of the electron deficiency and presence of a good leaving group. In this review, we focus on the three-component ring transformation (TCRT) of dinitropyridone involving a ketone and a n...
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| Veröffentlicht in: | Molecules (Basel, Switzerland) Switzerland), 2021-01, Vol.26 (3), p.639 |
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| creator | Le, Song Thi Asahara, Haruyasu Nishiwaki, Nagatoshi |
| description | 1-Methyl-3,5-dinitro-2-pyridone serves as an excellent substrate for nucleophilic-type ring transformation because of the electron deficiency and presence of a good leaving group. In this review, we focus on the three-component ring transformation (TCRT) of dinitropyridone involving a ketone and a nitrogen source. When dinitropyridone is allowed to react with a ketone in the presence of ammonia, TCRT proceeds to afford nitropyridines that are not easily produced by alternative procedures. Ammonium acetate can be used as a nitrogen source instead of ammonia to undergo the TCRT, leading to nitroanilines in addition to nitropyridines. In these reactions, dinitropyridone serves as a safe synthetic equivalent of unstable nitromalonaldehyde. |
| doi_str_mv | 10.3390/molecules26030639 |
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In this review, we focus on the three-component ring transformation (TCRT) of dinitropyridone involving a ketone and a nitrogen source. When dinitropyridone is allowed to react with a ketone in the presence of ammonia, TCRT proceeds to afford nitropyridines that are not easily produced by alternative procedures. Ammonium acetate can be used as a nitrogen source instead of ammonia to undergo the TCRT, leading to nitroanilines in addition to nitropyridines. In these reactions, dinitropyridone serves as a safe synthetic equivalent of unstable nitromalonaldehyde.</description><identifier>ISSN: 1420-3049</identifier><identifier>EISSN: 1420-3049</identifier><identifier>DOI: 10.3390/molecules26030639</identifier><identifier>PMID: 33530612</identifier><language>eng</language><publisher>Switzerland: MDPI AG</publisher><subject>Acetic acid ; Ammonia ; Ammonium ; Ammonium acetate ; bicyclic intermediate ; dinitropyridone ; Ketones ; Ligands ; nitroaniline ; Nitrogen ; nitromalonaldehyde ; nitropyridine ; Reagents ; Review ; three-component ring transformation ; Transformations</subject><ispartof>Molecules (Basel, Switzerland), 2021-01, Vol.26 (3), p.639</ispartof><rights>2021. This work is licensed under http://creativecommons.org/licenses/by/3.0/ (the “License”). Notwithstanding the ProQuest Terms and Conditions, you may use this content in accordance with the terms of the License.</rights><rights>2021 by the authors. 2021</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c559t-e1cd51f45926a7b5398ff2dd2629eae836b200144c1616e488dd152a731580523</citedby><cites>FETCH-LOGICAL-c559t-e1cd51f45926a7b5398ff2dd2629eae836b200144c1616e488dd152a731580523</cites><orcidid>0000-0002-1808-7373 ; 0000-0002-6052-8697 ; 0000-0002-5357-9023</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC7865560/pdf/$$EPDF$$P50$$Gpubmedcentral$$Hfree_for_read</linktopdf><linktohtml>$$Uhttps://www.ncbi.nlm.nih.gov/pmc/articles/PMC7865560/$$EHTML$$P50$$Gpubmedcentral$$Hfree_for_read</linktohtml><link.rule.ids>230,314,727,780,784,864,885,2102,27924,27925,53791,53793</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/33530612$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Le, Song Thi</creatorcontrib><creatorcontrib>Asahara, Haruyasu</creatorcontrib><creatorcontrib>Nishiwaki, Nagatoshi</creatorcontrib><title>Synthesis of Nitroaromatic Compounds via Three-Component Ring Transformations</title><title>Molecules (Basel, Switzerland)</title><addtitle>Molecules</addtitle><description>1-Methyl-3,5-dinitro-2-pyridone serves as an excellent substrate for nucleophilic-type ring transformation because of the electron deficiency and presence of a good leaving group. 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In these reactions, dinitropyridone serves as a safe synthetic equivalent of unstable nitromalonaldehyde.</description><subject>Acetic acid</subject><subject>Ammonia</subject><subject>Ammonium</subject><subject>Ammonium acetate</subject><subject>bicyclic intermediate</subject><subject>dinitropyridone</subject><subject>Ketones</subject><subject>Ligands</subject><subject>nitroaniline</subject><subject>Nitrogen</subject><subject>nitromalonaldehyde</subject><subject>nitropyridine</subject><subject>Reagents</subject><subject>Review</subject><subject>three-component ring transformation</subject><subject>Transformations</subject><issn>1420-3049</issn><issn>1420-3049</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><sourceid>ABUWG</sourceid><sourceid>AFKRA</sourceid><sourceid>AZQEC</sourceid><sourceid>BENPR</sourceid><sourceid>CCPQU</sourceid><sourceid>DWQXO</sourceid><sourceid>DOA</sourceid><recordid>eNplkUtvEzEUhS0EoiXwA9igkdiwGep37A0SinhUaqlUwtry2NeJoxk72DOV-u-ZNKVqYWXr-pxPPvcg9Jbgj4xpfDbkHtzUQ6USMyyZfoZOCae4ZZjr54_uJ-hVrTuMKeFEvEQnjIlZT-gpuvx5m8Yt1FibHJofcSzZljzYMbpmlYd9npKvzU20zXpbANq7WYI0NtcxbZp1samGXA6GnOpr9CLYvsKb-3OBfn39sl59by-uvp2vPl-0Tgg9tkCcFyRwoam0y04wrUKg3lNJNVhQTHYUY8K5I5JI4Ep5TwS1S0aEwoKyBTo_cn22O7MvcbDl1mQbzd0gl42xZY7Qg9Haes-J944HDhh3HDvtuGBBdKBkmFmfjqz91A3g3Zyt2P4J9OlLiluzyTdmqaQQ8-IX6MM9oOTfE9TRDLE66HubIE_VUK4kEUwoMUvf_yPd5amkeVUHFSdqrvEAJEeVK7nWAuHhMwSbQ_Hmv-Jnz7vHKR4cf5tmfwBy1awL</recordid><startdate>20210126</startdate><enddate>20210126</enddate><creator>Le, Song Thi</creator><creator>Asahara, Haruyasu</creator><creator>Nishiwaki, Nagatoshi</creator><general>MDPI AG</general><general>MDPI</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>3V.</scope><scope>7X7</scope><scope>7XB</scope><scope>88E</scope><scope>8FI</scope><scope>8FJ</scope><scope>8FK</scope><scope>ABUWG</scope><scope>AFKRA</scope><scope>AZQEC</scope><scope>BENPR</scope><scope>CCPQU</scope><scope>DWQXO</scope><scope>FYUFA</scope><scope>GHDGH</scope><scope>K9.</scope><scope>M0S</scope><scope>M1P</scope><scope>PIMPY</scope><scope>PQEST</scope><scope>PQQKQ</scope><scope>PQUKI</scope><scope>PRINS</scope><scope>7X8</scope><scope>5PM</scope><scope>DOA</scope><orcidid>https://orcid.org/0000-0002-1808-7373</orcidid><orcidid>https://orcid.org/0000-0002-6052-8697</orcidid><orcidid>https://orcid.org/0000-0002-5357-9023</orcidid></search><sort><creationdate>20210126</creationdate><title>Synthesis of Nitroaromatic Compounds via Three-Component Ring Transformations</title><author>Le, Song Thi ; Asahara, Haruyasu ; Nishiwaki, Nagatoshi</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c559t-e1cd51f45926a7b5398ff2dd2629eae836b200144c1616e488dd152a731580523</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Acetic acid</topic><topic>Ammonia</topic><topic>Ammonium</topic><topic>Ammonium acetate</topic><topic>bicyclic intermediate</topic><topic>dinitropyridone</topic><topic>Ketones</topic><topic>Ligands</topic><topic>nitroaniline</topic><topic>Nitrogen</topic><topic>nitromalonaldehyde</topic><topic>nitropyridine</topic><topic>Reagents</topic><topic>Review</topic><topic>three-component ring transformation</topic><topic>Transformations</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Le, Song Thi</creatorcontrib><creatorcontrib>Asahara, Haruyasu</creatorcontrib><creatorcontrib>Nishiwaki, Nagatoshi</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>ProQuest Central (Corporate)</collection><collection>Health & Medical Collection</collection><collection>ProQuest Central (purchase pre-March 2016)</collection><collection>Medical Database (Alumni Edition)</collection><collection>Hospital Premium Collection</collection><collection>Hospital Premium Collection (Alumni Edition)</collection><collection>ProQuest Central (Alumni) (purchase pre-March 2016)</collection><collection>ProQuest Central (Alumni Edition)</collection><collection>ProQuest Central UK/Ireland</collection><collection>ProQuest Central Essentials</collection><collection>ProQuest Central</collection><collection>ProQuest One Community College</collection><collection>ProQuest Central Korea</collection><collection>Health Research Premium Collection</collection><collection>Health Research Premium Collection (Alumni)</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>Health & Medical Collection (Alumni Edition)</collection><collection>Medical Database</collection><collection>Publicly Available Content Database</collection><collection>ProQuest One Academic Eastern Edition (DO NOT USE)</collection><collection>ProQuest One Academic</collection><collection>ProQuest One Academic UKI Edition</collection><collection>ProQuest Central China</collection><collection>MEDLINE - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><collection>DOAJ Directory of Open Access Journals</collection><jtitle>Molecules (Basel, Switzerland)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Le, Song Thi</au><au>Asahara, Haruyasu</au><au>Nishiwaki, Nagatoshi</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of Nitroaromatic Compounds via Three-Component Ring Transformations</atitle><jtitle>Molecules (Basel, Switzerland)</jtitle><addtitle>Molecules</addtitle><date>2021-01-26</date><risdate>2021</risdate><volume>26</volume><issue>3</issue><spage>639</spage><pages>639-</pages><issn>1420-3049</issn><eissn>1420-3049</eissn><abstract>1-Methyl-3,5-dinitro-2-pyridone serves as an excellent substrate for nucleophilic-type ring transformation because of the electron deficiency and presence of a good leaving group. In this review, we focus on the three-component ring transformation (TCRT) of dinitropyridone involving a ketone and a nitrogen source. When dinitropyridone is allowed to react with a ketone in the presence of ammonia, TCRT proceeds to afford nitropyridines that are not easily produced by alternative procedures. Ammonium acetate can be used as a nitrogen source instead of ammonia to undergo the TCRT, leading to nitroanilines in addition to nitropyridines. In these reactions, dinitropyridone serves as a safe synthetic equivalent of unstable nitromalonaldehyde.</abstract><cop>Switzerland</cop><pub>MDPI AG</pub><pmid>33530612</pmid><doi>10.3390/molecules26030639</doi><orcidid>https://orcid.org/0000-0002-1808-7373</orcidid><orcidid>https://orcid.org/0000-0002-6052-8697</orcidid><orcidid>https://orcid.org/0000-0002-5357-9023</orcidid><oa>free_for_read</oa></addata></record> |
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| subjects | Acetic acid Ammonia Ammonium Ammonium acetate bicyclic intermediate dinitropyridone Ketones Ligands nitroaniline Nitrogen nitromalonaldehyde nitropyridine Reagents Review three-component ring transformation Transformations |
| title | Synthesis of Nitroaromatic Compounds via Three-Component Ring Transformations |
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