Site‐Selective C–H Amidation of 2‐Aryl Quinazolinones Using Nitrene Surrogates
The site‐selective modifications of quinazolinones constitute a pivotal topic in drug discovery and material science. Herein, we describe the rhodium(III)‐catalyzed C–H amidation of 2‐aryl quinazolin‐4(3H)‐ones with a range of nitrene surrogates including dioxazolones, organic azides, and N‐methoxya...
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| Veröffentlicht in: | European journal of organic chemistry 2020-12, Vol.2020 (46), p.7134-7143 |
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| container_issue | 46 |
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| container_title | European journal of organic chemistry |
| container_volume | 2020 |
| creator | Kim, Saegun Jeoung, Daeun Kim, Kunyoung Lee, Seok Beom Lee, Suk Hun Park, Min Seo Ghosh, Prithwish Mishra, Neeraj Kumar Hong, Suckchang Kim, In Su |
| description | The site‐selective modifications of quinazolinones constitute a pivotal topic in drug discovery and material science. Herein, we describe the rhodium(III)‐catalyzed C–H amidation of 2‐aryl quinazolin‐4(3H)‐ones with a range of nitrene surrogates including dioxazolones, organic azides, and N‐methoxyamides. Complete site‐selectivity and functional group tolerance are observed. Notably, the large‐scale reaction and late‐stage functionalization highlight the synthetic potential of the developed protocol. Combined mechanistic investigations elucidate a plausible reaction mechanism of this process.
The site‐selective C–H amidation of 2‐aryl quinazolin‐4(3H)‐ones with dioxazolones under rhodium(III) catalysis is described. Gram‐scale reaction, late‐stage C–H functionalization, and synthetic transformations highlight the potential of the developed method. |
| doi_str_mv | 10.1002/ejoc.202001128 |
| format | Article |
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The site‐selective C–H amidation of 2‐aryl quinazolin‐4(3H)‐ones with dioxazolones under rhodium(III) catalysis is described. Gram‐scale reaction, late‐stage C–H functionalization, and synthetic transformations highlight the potential of the developed method.</description><identifier>ISSN: 1434-193X</identifier><identifier>EISSN: 1099-0690</identifier><identifier>DOI: 10.1002/ejoc.202001128</identifier><language>eng</language><publisher>Weinheim: Wiley Subscription Services, Inc</publisher><subject>Amidation ; Aromatic compounds ; Azides (organic) ; C–H functionalization ; Dioxazolones ; Functional groups ; Organometallic compounds ; Quinazolinoes ; Quinazolinones ; Reaction mechanisms ; Rhodium ; Selectivity</subject><ispartof>European journal of organic chemistry, 2020-12, Vol.2020 (46), p.7134-7143</ispartof><rights>2020 Wiley‐VCH GmbH</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3178-f3471c2650fbe933a4d44d9017d642eb4e733390f26bb21ec3da108a612ff7213</citedby><cites>FETCH-LOGICAL-c3178-f3471c2650fbe933a4d44d9017d642eb4e733390f26bb21ec3da108a612ff7213</cites><orcidid>0000-0002-2665-9431</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%2Fejoc.202001128$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fejoc.202001128$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids></links><search><creatorcontrib>Kim, Saegun</creatorcontrib><creatorcontrib>Jeoung, Daeun</creatorcontrib><creatorcontrib>Kim, Kunyoung</creatorcontrib><creatorcontrib>Lee, Seok Beom</creatorcontrib><creatorcontrib>Lee, Suk Hun</creatorcontrib><creatorcontrib>Park, Min Seo</creatorcontrib><creatorcontrib>Ghosh, Prithwish</creatorcontrib><creatorcontrib>Mishra, Neeraj Kumar</creatorcontrib><creatorcontrib>Hong, Suckchang</creatorcontrib><creatorcontrib>Kim, In Su</creatorcontrib><title>Site‐Selective C–H Amidation of 2‐Aryl Quinazolinones Using Nitrene Surrogates</title><title>European journal of organic chemistry</title><description>The site‐selective modifications of quinazolinones constitute a pivotal topic in drug discovery and material science. Herein, we describe the rhodium(III)‐catalyzed C–H amidation of 2‐aryl quinazolin‐4(3H)‐ones with a range of nitrene surrogates including dioxazolones, organic azides, and N‐methoxyamides. Complete site‐selectivity and functional group tolerance are observed. Notably, the large‐scale reaction and late‐stage functionalization highlight the synthetic potential of the developed protocol. Combined mechanistic investigations elucidate a plausible reaction mechanism of this process.
The site‐selective C–H amidation of 2‐aryl quinazolin‐4(3H)‐ones with dioxazolones under rhodium(III) catalysis is described. Gram‐scale reaction, late‐stage C–H functionalization, and synthetic transformations highlight the potential of the developed method.</description><subject>Amidation</subject><subject>Aromatic compounds</subject><subject>Azides (organic)</subject><subject>C–H functionalization</subject><subject>Dioxazolones</subject><subject>Functional groups</subject><subject>Organometallic compounds</subject><subject>Quinazolinoes</subject><subject>Quinazolinones</subject><subject>Reaction mechanisms</subject><subject>Rhodium</subject><subject>Selectivity</subject><issn>1434-193X</issn><issn>1099-0690</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><recordid>eNqFkE1Lw0AQQBdRsFavnhc8p85-NMkeS6hWKRZpC95CPmbLljRbd1OlnvoTBP9hf4kpFT16mjm8NwOPkGsGPQbAb3Fpix4HDsAYj09Ih4FSAYQKTttdChkwJV7OyYX3SwBQYcg6ZDY1De53n1OssGjMG9Jkv_sa0cHKlFljbE2tprwFBm5b0eeNqbMPW5na1ujp3Jt6QZ9M47BGOt04ZxdZg_6SnOms8nj1M7tkfjecJaNgPLl_SAbjoBAsigMtZMQKHvZB56iEyGQpZamARWUoOeYSIyGEAs3DPOcMC1FmDOIsZFzriDPRJTfHu2tnXzfom3RpN65uX6ZcRhCHsi-iluodqcJZ7x3qdO3MKnPblEF6KJceyqW_5VpBHYV3U-H2HzodPk6SP_cbKc90Nw</recordid><startdate>20201213</startdate><enddate>20201213</enddate><creator>Kim, Saegun</creator><creator>Jeoung, Daeun</creator><creator>Kim, Kunyoung</creator><creator>Lee, Seok Beom</creator><creator>Lee, Suk Hun</creator><creator>Park, Min Seo</creator><creator>Ghosh, Prithwish</creator><creator>Mishra, Neeraj Kumar</creator><creator>Hong, Suckchang</creator><creator>Kim, In Su</creator><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope><orcidid>https://orcid.org/0000-0002-2665-9431</orcidid></search><sort><creationdate>20201213</creationdate><title>Site‐Selective C–H Amidation of 2‐Aryl Quinazolinones Using Nitrene Surrogates</title><author>Kim, Saegun ; Jeoung, Daeun ; Kim, Kunyoung ; Lee, Seok Beom ; Lee, Suk Hun ; Park, Min Seo ; Ghosh, Prithwish ; Mishra, Neeraj Kumar ; Hong, Suckchang ; Kim, In Su</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3178-f3471c2650fbe933a4d44d9017d642eb4e733390f26bb21ec3da108a612ff7213</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Amidation</topic><topic>Aromatic compounds</topic><topic>Azides (organic)</topic><topic>C–H functionalization</topic><topic>Dioxazolones</topic><topic>Functional groups</topic><topic>Organometallic compounds</topic><topic>Quinazolinoes</topic><topic>Quinazolinones</topic><topic>Reaction mechanisms</topic><topic>Rhodium</topic><topic>Selectivity</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kim, Saegun</creatorcontrib><creatorcontrib>Jeoung, Daeun</creatorcontrib><creatorcontrib>Kim, Kunyoung</creatorcontrib><creatorcontrib>Lee, Seok Beom</creatorcontrib><creatorcontrib>Lee, Suk Hun</creatorcontrib><creatorcontrib>Park, Min Seo</creatorcontrib><creatorcontrib>Ghosh, Prithwish</creatorcontrib><creatorcontrib>Mishra, Neeraj Kumar</creatorcontrib><creatorcontrib>Hong, Suckchang</creatorcontrib><creatorcontrib>Kim, In Su</creatorcontrib><collection>CrossRef</collection><jtitle>European journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kim, Saegun</au><au>Jeoung, Daeun</au><au>Kim, Kunyoung</au><au>Lee, Seok Beom</au><au>Lee, Suk Hun</au><au>Park, Min Seo</au><au>Ghosh, Prithwish</au><au>Mishra, Neeraj Kumar</au><au>Hong, Suckchang</au><au>Kim, In Su</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Site‐Selective C–H Amidation of 2‐Aryl Quinazolinones Using Nitrene Surrogates</atitle><jtitle>European journal of organic chemistry</jtitle><date>2020-12-13</date><risdate>2020</risdate><volume>2020</volume><issue>46</issue><spage>7134</spage><epage>7143</epage><pages>7134-7143</pages><issn>1434-193X</issn><eissn>1099-0690</eissn><abstract>The site‐selective modifications of quinazolinones constitute a pivotal topic in drug discovery and material science. Herein, we describe the rhodium(III)‐catalyzed C–H amidation of 2‐aryl quinazolin‐4(3H)‐ones with a range of nitrene surrogates including dioxazolones, organic azides, and N‐methoxyamides. Complete site‐selectivity and functional group tolerance are observed. Notably, the large‐scale reaction and late‐stage functionalization highlight the synthetic potential of the developed protocol. Combined mechanistic investigations elucidate a plausible reaction mechanism of this process.
The site‐selective C–H amidation of 2‐aryl quinazolin‐4(3H)‐ones with dioxazolones under rhodium(III) catalysis is described. Gram‐scale reaction, late‐stage C–H functionalization, and synthetic transformations highlight the potential of the developed method.</abstract><cop>Weinheim</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/ejoc.202001128</doi><tpages>10</tpages><orcidid>https://orcid.org/0000-0002-2665-9431</orcidid></addata></record> |
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| language | eng |
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| subjects | Amidation Aromatic compounds Azides (organic) C–H functionalization Dioxazolones Functional groups Organometallic compounds Quinazolinoes Quinazolinones Reaction mechanisms Rhodium Selectivity |
| title | Site‐Selective C–H Amidation of 2‐Aryl Quinazolinones Using Nitrene Surrogates |
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