Copper‐Catalyzed C(sp3)− Functionalization and Annulation of 2‐Bromoaryl Oximes with Active Methylene Compounds towards Synthesis of Isoquinoline N‐Oxides
The established process proceeds through copper (II)‐catalyzed C(sp3)− functionalization of β‐diketones/β‐ketoesters with 2‐bromobenzaldehyde oximes followed by the intramolecular cyclization of in situ generated acylated intermediates to deliver isoquinoline N‐oxides. The copper(II) acetate catalyz...
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| Veröffentlicht in: | Advanced synthesis & catalysis 2023-07, Vol.365 (13), p.2203-2210 |
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| container_title | Advanced synthesis & catalysis |
| container_volume | 365 |
| creator | Patel, Chandresh K. Gujjarappa, Raghuram Kant, Kamal Ghanta, Susanta Singh, Virender Kabi, Arup K. Al‐Zaqri, Nabil Malakar, Chandi C. |
| description | The established process proceeds through copper (II)‐catalyzed C(sp3)− functionalization of β‐diketones/β‐ketoesters with 2‐bromobenzaldehyde oximes followed by the intramolecular cyclization of in situ generated acylated intermediates to deliver isoquinoline N‐oxides. The copper(II) acetate catalyzed C−H functionalization showed maximum efficacy at 60 °C in methanol/toluene as solvent. The described reaction conditions were applicable over a wide range of substrates with a variety of functional groups to yield isoquinoline N‐oxides in yields up to 85%. The developed approach was further elucidated by means of control experiments and DFT calculations. |
| doi_str_mv | 10.1002/adsc.202300217 |
| format | Article |
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The copper(II) acetate catalyzed C−H functionalization showed maximum efficacy at 60 °C in methanol/toluene as solvent. The described reaction conditions were applicable over a wide range of substrates with a variety of functional groups to yield isoquinoline N‐oxides in yields up to 85%. The developed approach was further elucidated by means of control experiments and DFT calculations.</description><identifier>ISSN: 1615-4150</identifier><identifier>EISSN: 1615-4169</identifier><identifier>DOI: 10.1002/adsc.202300217</identifier><language>eng</language><publisher>Heidelberg: Wiley Subscription Services, Inc</publisher><subject>Active methylene compounds ; C(sp3)− activation ; Chemical reactions ; Copper acetate ; Copper catalysis ; Diketones ; Functional groups ; Isoquinoline N-oxide ; Oxides ; Oximes ; Substrates ; Toluene ; trans-esterification</subject><ispartof>Advanced synthesis & catalysis, 2023-07, Vol.365 (13), p.2203-2210</ispartof><rights>2023 Wiley‐VCH GmbH</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3177-60ee0e4f11428064d61536766331be8b71afd7adc3b64510a2f2588cd08bbca73</citedby><cites>FETCH-LOGICAL-c3177-60ee0e4f11428064d61536766331be8b71afd7adc3b64510a2f2588cd08bbca73</cites><orcidid>0000-0003-4242-5421 ; 0000-0002-2586-3190 ; 0000-0002-9478-017X</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fadsc.202300217$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fadsc.202300217$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,777,781,1412,27905,27906,45555,45556</link.rule.ids></links><search><creatorcontrib>Patel, Chandresh K.</creatorcontrib><creatorcontrib>Gujjarappa, Raghuram</creatorcontrib><creatorcontrib>Kant, Kamal</creatorcontrib><creatorcontrib>Ghanta, Susanta</creatorcontrib><creatorcontrib>Singh, Virender</creatorcontrib><creatorcontrib>Kabi, Arup K.</creatorcontrib><creatorcontrib>Al‐Zaqri, Nabil</creatorcontrib><creatorcontrib>Malakar, Chandi C.</creatorcontrib><title>Copper‐Catalyzed C(sp3)− Functionalization and Annulation of 2‐Bromoaryl Oximes with Active Methylene Compounds towards Synthesis of Isoquinoline N‐Oxides</title><title>Advanced synthesis & catalysis</title><description>The established process proceeds through copper (II)‐catalyzed C(sp3)− functionalization of β‐diketones/β‐ketoesters with 2‐bromobenzaldehyde oximes followed by the intramolecular cyclization of in situ generated acylated intermediates to deliver isoquinoline N‐oxides. The copper(II) acetate catalyzed C−H functionalization showed maximum efficacy at 60 °C in methanol/toluene as solvent. The described reaction conditions were applicable over a wide range of substrates with a variety of functional groups to yield isoquinoline N‐oxides in yields up to 85%. The developed approach was further elucidated by means of control experiments and DFT calculations.</description><subject>Active methylene compounds</subject><subject>C(sp3)− activation</subject><subject>Chemical reactions</subject><subject>Copper acetate</subject><subject>Copper catalysis</subject><subject>Diketones</subject><subject>Functional groups</subject><subject>Isoquinoline N-oxide</subject><subject>Oxides</subject><subject>Oximes</subject><subject>Substrates</subject><subject>Toluene</subject><subject>trans-esterification</subject><issn>1615-4150</issn><issn>1615-4169</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><recordid>eNqFkTtPwzAUhSMEEs-V2RILDC1-JHYYS3hV4jEAc-TEN6pRagc7oaQTIyPiJ_DT-ktwVQQj071XOt_RPTpRtE_wkGBMj6Xy5ZBiysJBxFq0RThJBjHhJ-u_e4I3o23vnzAmIhViK_rKbNOAW7x9ZLKVdT8HhbJD37CjxfsnuuhM2WprZK3ncrkgaRQaGdPVq9NWiAb21Nmpla6v0d2rnoJHM91O0CiwL4BuoJ30NRhAmZ02tjPKo9bOpAvzvjftBLz2S6ext8-dNrbWQXsbbIOZAr8bbVSy9rD3M3eix4vzh-xqcH13Oc5G14OSESEGHANgiCtCYppiHquQmHHBOWOkgLQQRFZKSFWygscJwZJWNEnTUuG0KEop2E50sPJtXPgDfJs_2c6F7D6nKUu4oCnBQTVcqUpnvXdQ5Y3T05A9Jzhf9pAve8h_ewjAyQqY6Rr6f9T56Ow--2O_AXAnkq8</recordid><startdate>20230704</startdate><enddate>20230704</enddate><creator>Patel, Chandresh K.</creator><creator>Gujjarappa, Raghuram</creator><creator>Kant, Kamal</creator><creator>Ghanta, Susanta</creator><creator>Singh, Virender</creator><creator>Kabi, Arup K.</creator><creator>Al‐Zaqri, Nabil</creator><creator>Malakar, Chandi C.</creator><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7U5</scope><scope>8FD</scope><scope>L7M</scope><orcidid>https://orcid.org/0000-0003-4242-5421</orcidid><orcidid>https://orcid.org/0000-0002-2586-3190</orcidid><orcidid>https://orcid.org/0000-0002-9478-017X</orcidid></search><sort><creationdate>20230704</creationdate><title>Copper‐Catalyzed C(sp3)− Functionalization and Annulation of 2‐Bromoaryl Oximes with Active Methylene Compounds towards Synthesis of Isoquinoline N‐Oxides</title><author>Patel, Chandresh K. ; Gujjarappa, Raghuram ; Kant, Kamal ; Ghanta, Susanta ; Singh, Virender ; Kabi, Arup K. ; Al‐Zaqri, Nabil ; Malakar, Chandi C.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3177-60ee0e4f11428064d61536766331be8b71afd7adc3b64510a2f2588cd08bbca73</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><topic>Active methylene compounds</topic><topic>C(sp3)− activation</topic><topic>Chemical reactions</topic><topic>Copper acetate</topic><topic>Copper catalysis</topic><topic>Diketones</topic><topic>Functional groups</topic><topic>Isoquinoline N-oxide</topic><topic>Oxides</topic><topic>Oximes</topic><topic>Substrates</topic><topic>Toluene</topic><topic>trans-esterification</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Patel, Chandresh K.</creatorcontrib><creatorcontrib>Gujjarappa, Raghuram</creatorcontrib><creatorcontrib>Kant, Kamal</creatorcontrib><creatorcontrib>Ghanta, Susanta</creatorcontrib><creatorcontrib>Singh, Virender</creatorcontrib><creatorcontrib>Kabi, Arup K.</creatorcontrib><creatorcontrib>Al‐Zaqri, Nabil</creatorcontrib><creatorcontrib>Malakar, Chandi C.</creatorcontrib><collection>CrossRef</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>Technology Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Advanced synthesis & catalysis</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Patel, Chandresh K.</au><au>Gujjarappa, Raghuram</au><au>Kant, Kamal</au><au>Ghanta, Susanta</au><au>Singh, Virender</au><au>Kabi, Arup K.</au><au>Al‐Zaqri, Nabil</au><au>Malakar, Chandi C.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Copper‐Catalyzed C(sp3)− Functionalization and Annulation of 2‐Bromoaryl Oximes with Active Methylene Compounds towards Synthesis of Isoquinoline N‐Oxides</atitle><jtitle>Advanced synthesis & catalysis</jtitle><date>2023-07-04</date><risdate>2023</risdate><volume>365</volume><issue>13</issue><spage>2203</spage><epage>2210</epage><pages>2203-2210</pages><issn>1615-4150</issn><eissn>1615-4169</eissn><abstract>The established process proceeds through copper (II)‐catalyzed C(sp3)− functionalization of β‐diketones/β‐ketoesters with 2‐bromobenzaldehyde oximes followed by the intramolecular cyclization of in situ generated acylated intermediates to deliver isoquinoline N‐oxides. The copper(II) acetate catalyzed C−H functionalization showed maximum efficacy at 60 °C in methanol/toluene as solvent. The described reaction conditions were applicable over a wide range of substrates with a variety of functional groups to yield isoquinoline N‐oxides in yields up to 85%. The developed approach was further elucidated by means of control experiments and DFT calculations.</abstract><cop>Heidelberg</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/adsc.202300217</doi><tpages>8</tpages><orcidid>https://orcid.org/0000-0003-4242-5421</orcidid><orcidid>https://orcid.org/0000-0002-2586-3190</orcidid><orcidid>https://orcid.org/0000-0002-9478-017X</orcidid></addata></record> |
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| source | Wiley Online Library Journals Frontfile Complete |
| subjects | Active methylene compounds C(sp3)− activation Chemical reactions Copper acetate Copper catalysis Diketones Functional groups Isoquinoline N-oxide Oxides Oximes Substrates Toluene trans-esterification |
| title | Copper‐Catalyzed C(sp3)− Functionalization and Annulation of 2‐Bromoaryl Oximes with Active Methylene Compounds towards Synthesis of Isoquinoline N‐Oxides |
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