Ru()-Catalyzed C-H addition and oxidative cyclization of 2-aryl quinazolinones with activated aldehydes
The ruthenium( ii )-catalyzed cross-coupling reaction between 2-aryl quinazolinones and activated aldehydes is described. This method enables the site-selective hydroxyalkylation under redox-neutral conditions. Moreover, this protocol provides a facile access to various tetracyclic isoindoloquinazol...
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| Veröffentlicht in: | Organic & biomolecular chemistry 2020-12, Vol.18 (47), p.9611-9622 |
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| container_title | Organic & biomolecular chemistry |
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| creator | Choi, Jin Ho Kim, Kunyoung Oh, Harin Han, Sangil Mishra, Neeraj Kumar Kim, In Su |
| description | The ruthenium(
ii
)-catalyzed cross-coupling reaction between 2-aryl quinazolinones and activated aldehydes is described. This method enables the site-selective hydroxyalkylation under redox-neutral conditions. Moreover, this protocol provides a facile access to various tetracyclic isoindoloquinazolinones by using Cu(OAc)
2
as an external oxidant
via
C-H addition and subsequent intramolecular cyclization. A wide substrate scope and a high level of chemoselectivity as well as broad functional group tolerance are observed.
The ruthenium(
ii
)-catalyzed cross-coupling reaction between 2-aryl quinazolinones and activated aldehydes under redox-neutral and oxidative conditions is described. |
| doi_str_mv | 10.1039/d0ob01663b |
| format | Article |
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ii
)-catalyzed cross-coupling reaction between 2-aryl quinazolinones and activated aldehydes is described. This method enables the site-selective hydroxyalkylation under redox-neutral conditions. Moreover, this protocol provides a facile access to various tetracyclic isoindoloquinazolinones by using Cu(OAc)
2
as an external oxidant
via
C-H addition and subsequent intramolecular cyclization. A wide substrate scope and a high level of chemoselectivity as well as broad functional group tolerance are observed.
The ruthenium(
ii
)-catalyzed cross-coupling reaction between 2-aryl quinazolinones and activated aldehydes under redox-neutral and oxidative conditions is described.</description><identifier>ISSN: 1477-0520</identifier><identifier>EISSN: 1477-0539</identifier><identifier>DOI: 10.1039/d0ob01663b</identifier><identifier>PMID: 33020797</identifier><language>eng</language><publisher>England: Royal Society of Chemistry</publisher><subject>Aldehydes ; Aromatic compounds ; Chemical reactions ; Cross coupling ; Crystallography ; Functional groups ; NMR ; Nuclear magnetic resonance ; Oxidants ; Oxidizing agents ; Quinazolinones ; Ruthenium ; Ruthenium compounds ; Substrates</subject><ispartof>Organic & biomolecular chemistry, 2020-12, Vol.18 (47), p.9611-9622</ispartof><rights>Copyright Royal Society of Chemistry 2020</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c337t-18b7a465e2f9047215a013a5e14224474f60924f8f4e574f8d7f1e770132279f3</citedby><cites>FETCH-LOGICAL-c337t-18b7a465e2f9047215a013a5e14224474f60924f8f4e574f8d7f1e770132279f3</cites><orcidid>0000-0002-2665-9431</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/33020797$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Choi, Jin Ho</creatorcontrib><creatorcontrib>Kim, Kunyoung</creatorcontrib><creatorcontrib>Oh, Harin</creatorcontrib><creatorcontrib>Han, Sangil</creatorcontrib><creatorcontrib>Mishra, Neeraj Kumar</creatorcontrib><creatorcontrib>Kim, In Su</creatorcontrib><title>Ru()-Catalyzed C-H addition and oxidative cyclization of 2-aryl quinazolinones with activated aldehydes</title><title>Organic & biomolecular chemistry</title><addtitle>Org Biomol Chem</addtitle><description>The ruthenium(
ii
)-catalyzed cross-coupling reaction between 2-aryl quinazolinones and activated aldehydes is described. This method enables the site-selective hydroxyalkylation under redox-neutral conditions. Moreover, this protocol provides a facile access to various tetracyclic isoindoloquinazolinones by using Cu(OAc)
2
as an external oxidant
via
C-H addition and subsequent intramolecular cyclization. A wide substrate scope and a high level of chemoselectivity as well as broad functional group tolerance are observed.
The ruthenium(
ii
)-catalyzed cross-coupling reaction between 2-aryl quinazolinones and activated aldehydes under redox-neutral and oxidative conditions is described.</description><subject>Aldehydes</subject><subject>Aromatic compounds</subject><subject>Chemical reactions</subject><subject>Cross coupling</subject><subject>Crystallography</subject><subject>Functional groups</subject><subject>NMR</subject><subject>Nuclear magnetic resonance</subject><subject>Oxidants</subject><subject>Oxidizing agents</subject><subject>Quinazolinones</subject><subject>Ruthenium</subject><subject>Ruthenium compounds</subject><subject>Substrates</subject><issn>1477-0520</issn><issn>1477-0539</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><recordid>eNpdkU1PwzAMhiMEYjC4cAdF4jKQCs5Hm_bIxseQJk1CcK6yJmGZugaaFth-PWEbQ-JkW378yn6N0AmBKwIsu1bgJkCShE120AHhQkQQs2x3m1PooEPvZwAkEwnfRx3GgILIxAF6fWp7F9FANrJcLLXCg2iIpVK2sa7CslLYfVklG_uhcbEoSruUq44zmEayXpT4vbWVXLrSVq7SHn_aZoplEQZkE-RkqfR0obQ_QntGll4fb2IXvdzfPQ-G0Wj88Di4GUUFY6KJSDoRkiexpiYDLiiJJRAmY004pZwLbhLIKDep4ToOVaqEIVqIAFEqMsO6qLfWfavde6t9k8-tL3RZykq71udBJE1jAsG4Ljr_h85cW1dhu0AJiHkSVgrU5Zoqaud9rU3-Vtt5OD0nkP_Yn9_CuL-yvx_gs41kO5lrtUV__Q7A6RqofbHt_v2PfQNypoeQ</recordid><startdate>20201221</startdate><enddate>20201221</enddate><creator>Choi, Jin Ho</creator><creator>Kim, Kunyoung</creator><creator>Oh, Harin</creator><creator>Han, Sangil</creator><creator>Mishra, Neeraj Kumar</creator><creator>Kim, In Su</creator><general>Royal Society of Chemistry</general><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7QO</scope><scope>7T7</scope><scope>7TM</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>P64</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-2665-9431</orcidid></search><sort><creationdate>20201221</creationdate><title>Ru()-Catalyzed C-H addition and oxidative cyclization of 2-aryl quinazolinones with activated aldehydes</title><author>Choi, Jin Ho ; Kim, Kunyoung ; Oh, Harin ; Han, Sangil ; Mishra, Neeraj Kumar ; Kim, In Su</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c337t-18b7a465e2f9047215a013a5e14224474f60924f8f4e574f8d7f1e770132279f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Aldehydes</topic><topic>Aromatic compounds</topic><topic>Chemical reactions</topic><topic>Cross coupling</topic><topic>Crystallography</topic><topic>Functional groups</topic><topic>NMR</topic><topic>Nuclear magnetic resonance</topic><topic>Oxidants</topic><topic>Oxidizing agents</topic><topic>Quinazolinones</topic><topic>Ruthenium</topic><topic>Ruthenium compounds</topic><topic>Substrates</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Choi, Jin Ho</creatorcontrib><creatorcontrib>Kim, Kunyoung</creatorcontrib><creatorcontrib>Oh, Harin</creatorcontrib><creatorcontrib>Han, Sangil</creatorcontrib><creatorcontrib>Mishra, Neeraj Kumar</creatorcontrib><creatorcontrib>Kim, In Su</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><collection>Biotechnology Research Abstracts</collection><collection>Industrial and Applied Microbiology Abstracts (Microbiology A)</collection><collection>Nucleic Acids Abstracts</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Organic & biomolecular chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Choi, Jin Ho</au><au>Kim, Kunyoung</au><au>Oh, Harin</au><au>Han, Sangil</au><au>Mishra, Neeraj Kumar</au><au>Kim, In Su</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Ru()-Catalyzed C-H addition and oxidative cyclization of 2-aryl quinazolinones with activated aldehydes</atitle><jtitle>Organic & biomolecular chemistry</jtitle><addtitle>Org Biomol Chem</addtitle><date>2020-12-21</date><risdate>2020</risdate><volume>18</volume><issue>47</issue><spage>9611</spage><epage>9622</epage><pages>9611-9622</pages><issn>1477-0520</issn><eissn>1477-0539</eissn><abstract>The ruthenium(
ii
)-catalyzed cross-coupling reaction between 2-aryl quinazolinones and activated aldehydes is described. This method enables the site-selective hydroxyalkylation under redox-neutral conditions. Moreover, this protocol provides a facile access to various tetracyclic isoindoloquinazolinones by using Cu(OAc)
2
as an external oxidant
via
C-H addition and subsequent intramolecular cyclization. A wide substrate scope and a high level of chemoselectivity as well as broad functional group tolerance are observed.
The ruthenium(
ii
)-catalyzed cross-coupling reaction between 2-aryl quinazolinones and activated aldehydes under redox-neutral and oxidative conditions is described.</abstract><cop>England</cop><pub>Royal Society of Chemistry</pub><pmid>33020797</pmid><doi>10.1039/d0ob01663b</doi><tpages>12</tpages><orcidid>https://orcid.org/0000-0002-2665-9431</orcidid></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 1477-0520 |
| ispartof | Organic & biomolecular chemistry, 2020-12, Vol.18 (47), p.9611-9622 |
| issn | 1477-0520 1477-0539 |
| language | eng |
| recordid | cdi_crossref_primary_10_1039_D0OB01663B |
| source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Aldehydes Aromatic compounds Chemical reactions Cross coupling Crystallography Functional groups NMR Nuclear magnetic resonance Oxidants Oxidizing agents Quinazolinones Ruthenium Ruthenium compounds Substrates |
| title | Ru()-Catalyzed C-H addition and oxidative cyclization of 2-aryl quinazolinones with activated aldehydes |
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