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Efficient Synthesis of Quinazolines from Aryl Imidates and N‐Alkoxyamide by Ir(III)‐Catalyzed C−H Amidation/Cyclization
An Ir(III) catalyst was used for the first time to realize the synthesis of quinazolines by C−H bond activation/cyclization with N‐alkoxyamides as amidation reagents. This reaction has the advantages of wide substrate adaptability, good to excellent yields under mild conditions, short reaction times...
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Published in: | European journal of organic chemistry 2021-08, Vol.2021 (29), p.4144-4147 |
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container_end_page | 4147 |
container_issue | 29 |
container_start_page | 4144 |
container_title | European journal of organic chemistry |
container_volume | 2021 |
creator | Fan, Wei‐Tai Huang, Zhibin Xu, Xu Tu, Guangliang Geng, Jingyao Ji, Shun‐Jun Zhao, Yingsheng |
description | An Ir(III) catalyst was used for the first time to realize the synthesis of quinazolines by C−H bond activation/cyclization with N‐alkoxyamides as amidation reagents. This reaction has the advantages of wide substrate adaptability, good to excellent yields under mild conditions, short reaction times, and no need for an inert atmosphere. Importantly, several quinazolines from bioactive compounds were obtained, which highlights the importance of this new method.
We developed an unprecedented iridium‐catalyzed C−H activation/cyclization to synthesize isoquinoline compounds efficiently using ethyl benzimidate and N‐alkoxyamides. This reaction has the advantages of wide substrate adaptability, short reaction times and no need for an inert atmosphere. In addition, some drug molecules smoothly converted into aminating reagents, reacted efficiently and afforded molecules with potential drug activity. |
doi_str_mv | 10.1002/ejoc.202100726 |
format | article |
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We developed an unprecedented iridium‐catalyzed C−H activation/cyclization to synthesize isoquinoline compounds efficiently using ethyl benzimidate and N‐alkoxyamides. This reaction has the advantages of wide substrate adaptability, short reaction times and no need for an inert atmosphere. In addition, some drug molecules smoothly converted into aminating reagents, reacted efficiently and afforded molecules with potential drug activity.</description><identifier>ISSN: 1434-193X</identifier><identifier>EISSN: 1099-0690</identifier><identifier>DOI: 10.1002/ejoc.202100726</identifier><language>eng</language><publisher>Weinheim: Wiley Subscription Services, Inc</publisher><subject>Bioactive compounds ; Cyclization ; C−H activation ; Hydrogen bonds ; Inert atmospheres ; Ir(III)-catalyzed ; Quinazolines ; Reagents ; Substrates</subject><ispartof>European journal of organic chemistry, 2021-08, Vol.2021 (29), p.4144-4147</ispartof><rights>2021 Wiley‐VCH GmbH</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3176-15bdf6301fece7ff2d1cde41de0e1b8465f38accc3528c70d7535fce91ae7c553</citedby><cites>FETCH-LOGICAL-c3176-15bdf6301fece7ff2d1cde41de0e1b8465f38accc3528c70d7535fce91ae7c553</cites><orcidid>0000-0002-6142-7839</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></links><search><creatorcontrib>Fan, Wei‐Tai</creatorcontrib><creatorcontrib>Huang, Zhibin</creatorcontrib><creatorcontrib>Xu, Xu</creatorcontrib><creatorcontrib>Tu, Guangliang</creatorcontrib><creatorcontrib>Geng, Jingyao</creatorcontrib><creatorcontrib>Ji, Shun‐Jun</creatorcontrib><creatorcontrib>Zhao, Yingsheng</creatorcontrib><title>Efficient Synthesis of Quinazolines from Aryl Imidates and N‐Alkoxyamide by Ir(III)‐Catalyzed C−H Amidation/Cyclization</title><title>European journal of organic chemistry</title><description>An Ir(III) catalyst was used for the first time to realize the synthesis of quinazolines by C−H bond activation/cyclization with N‐alkoxyamides as amidation reagents. This reaction has the advantages of wide substrate adaptability, good to excellent yields under mild conditions, short reaction times, and no need for an inert atmosphere. Importantly, several quinazolines from bioactive compounds were obtained, which highlights the importance of this new method.
We developed an unprecedented iridium‐catalyzed C−H activation/cyclization to synthesize isoquinoline compounds efficiently using ethyl benzimidate and N‐alkoxyamides. This reaction has the advantages of wide substrate adaptability, short reaction times and no need for an inert atmosphere. In addition, some drug molecules smoothly converted into aminating reagents, reacted efficiently and afforded molecules with potential drug activity.</description><subject>Bioactive compounds</subject><subject>Cyclization</subject><subject>C−H activation</subject><subject>Hydrogen bonds</subject><subject>Inert atmospheres</subject><subject>Ir(III)-catalyzed</subject><subject>Quinazolines</subject><subject>Reagents</subject><subject>Substrates</subject><issn>1434-193X</issn><issn>1099-0690</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><recordid>eNqFkE9LAzEQxYMoWKtXzwEvetg22ezfY1mqXSkWUcFbSLMTTN1uNNmiWxA8ehQ_Yj-J21b06Glm3rzfDDyEjinpUUL8PsyM7PnEb4fYj3ZQh5I09UiUkt22D1jg0ZTd76MD52aEkDSKaAe9DZXSUkNV45umqh_AaYeNwtcLXYmlKXUFDitr5nhgmxLnc12IupVEVeCr1fvnoHw0r41oZcDTBuf2NM_zs3aRiVqUzRIKnK0-vkZ4sCG1qfpZI0u93PSHaE-J0sHRT-2iu_PhbTbyxpOLPBuMPcloHHk0nBYqYoQqkBAr5RdUFhDQAgjQaRJEoWKJkFKy0E9kTIo4ZKGSkFIBsQxD1kUn27tP1jwvwNV8Zha2al9yP4wYS2hMaOvqbV3SGucsKP5k9VzYhlPC1xHzdcT8N-IWSLfAiy6h-cfNh5eT7I_9BsJrhH0</recordid><startdate>20210806</startdate><enddate>20210806</enddate><creator>Fan, Wei‐Tai</creator><creator>Huang, Zhibin</creator><creator>Xu, Xu</creator><creator>Tu, Guangliang</creator><creator>Geng, Jingyao</creator><creator>Ji, Shun‐Jun</creator><creator>Zhao, Yingsheng</creator><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope><orcidid>https://orcid.org/0000-0002-6142-7839</orcidid></search><sort><creationdate>20210806</creationdate><title>Efficient Synthesis of Quinazolines from Aryl Imidates and N‐Alkoxyamide by Ir(III)‐Catalyzed C−H Amidation/Cyclization</title><author>Fan, Wei‐Tai ; Huang, Zhibin ; Xu, Xu ; Tu, Guangliang ; Geng, Jingyao ; Ji, Shun‐Jun ; Zhao, Yingsheng</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3176-15bdf6301fece7ff2d1cde41de0e1b8465f38accc3528c70d7535fce91ae7c553</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Bioactive compounds</topic><topic>Cyclization</topic><topic>C−H activation</topic><topic>Hydrogen bonds</topic><topic>Inert atmospheres</topic><topic>Ir(III)-catalyzed</topic><topic>Quinazolines</topic><topic>Reagents</topic><topic>Substrates</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Fan, Wei‐Tai</creatorcontrib><creatorcontrib>Huang, Zhibin</creatorcontrib><creatorcontrib>Xu, Xu</creatorcontrib><creatorcontrib>Tu, Guangliang</creatorcontrib><creatorcontrib>Geng, Jingyao</creatorcontrib><creatorcontrib>Ji, Shun‐Jun</creatorcontrib><creatorcontrib>Zhao, Yingsheng</creatorcontrib><collection>CrossRef</collection><jtitle>European journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Fan, Wei‐Tai</au><au>Huang, Zhibin</au><au>Xu, Xu</au><au>Tu, Guangliang</au><au>Geng, Jingyao</au><au>Ji, Shun‐Jun</au><au>Zhao, Yingsheng</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Efficient Synthesis of Quinazolines from Aryl Imidates and N‐Alkoxyamide by Ir(III)‐Catalyzed C−H Amidation/Cyclization</atitle><jtitle>European journal of organic chemistry</jtitle><date>2021-08-06</date><risdate>2021</risdate><volume>2021</volume><issue>29</issue><spage>4144</spage><epage>4147</epage><pages>4144-4147</pages><issn>1434-193X</issn><eissn>1099-0690</eissn><abstract>An Ir(III) catalyst was used for the first time to realize the synthesis of quinazolines by C−H bond activation/cyclization with N‐alkoxyamides as amidation reagents. This reaction has the advantages of wide substrate adaptability, good to excellent yields under mild conditions, short reaction times, and no need for an inert atmosphere. Importantly, several quinazolines from bioactive compounds were obtained, which highlights the importance of this new method.
We developed an unprecedented iridium‐catalyzed C−H activation/cyclization to synthesize isoquinoline compounds efficiently using ethyl benzimidate and N‐alkoxyamides. This reaction has the advantages of wide substrate adaptability, short reaction times and no need for an inert atmosphere. In addition, some drug molecules smoothly converted into aminating reagents, reacted efficiently and afforded molecules with potential drug activity.</abstract><cop>Weinheim</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/ejoc.202100726</doi><tpages>4</tpages><orcidid>https://orcid.org/0000-0002-6142-7839</orcidid></addata></record> |
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source | Wiley |
subjects | Bioactive compounds Cyclization C−H activation Hydrogen bonds Inert atmospheres Ir(III)-catalyzed Quinazolines Reagents Substrates |
title | Efficient Synthesis of Quinazolines from Aryl Imidates and N‐Alkoxyamide by Ir(III)‐Catalyzed C−H Amidation/Cyclization |
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