Synthesis of Indole‐Fused Pyrazino[1,2‐a]quinazolinones by Copper(I)‐Catalyzed Selective Hydroamination‐Cyclization of Alkynyl‐tethered Quinazolinones
We described a copper(I)‐catalyzed atom economic and selective hydroamination‐cyclization of alkynyl‐tethered quinazolinones to prepare a variety of indole‐fused pyrazino[1,2‐a]quinazolinones in good to excellent yields ranging from 39 %–99 % under mild reaction conditions. Control experiments revea...
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| Veröffentlicht in: | Chemistry : a European journal 2024-09, Vol.30 (50), p.e202402085-n/a |
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| creator | Liu, Xiao‐Qing Chen, Yan‐Jie Zou, Pei‐Sen Su, Jun‐Cheng Pan, Cheng‐Xue Mo, Dong‐Liang Su, Gui‐Fa |
| description | We described a copper(I)‐catalyzed atom economic and selective hydroamination‐cyclization of alkynyl‐tethered quinazolinones to prepare a variety of indole‐fused pyrazino[1,2‐a]quinazolinones in good to excellent yields ranging from 39 %–99 % under mild reaction conditions. Control experiments revealed that coordination‐directed method of quinazolinone moiety with copper(I) was important for the selective hydroamination‐cyclization of alkynes at the N1‐atom instead of N3‐atom of quinazolinone. The reaction could be easily performed at gram scales and some prepared indole‐fused pyrazino[1,2‐a]quinazolinones with donating groups on the indole moiety showed a distinct fluorescence emission wavelength with blue shift under the acid conditions.
We described a copper(I)‐catalyzed atom‐economic and highly chemo‐selective hydroamination‐cyclization of alkynyl‐tethered quinazolinones to prepare a variety of indole‐fused pyrazino[1,2‐a]quinazolinones in good to excellent yields under mild reaction conditions. |
| doi_str_mv | 10.1002/chem.202402085 |
| format | Article |
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We described a copper(I)‐catalyzed atom‐economic and highly chemo‐selective hydroamination‐cyclization of alkynyl‐tethered quinazolinones to prepare a variety of indole‐fused pyrazino[1,2‐a]quinazolinones in good to excellent yields under mild reaction conditions.</description><identifier>ISSN: 0947-6539</identifier><identifier>EISSN: 1521-3765</identifier><identifier>DOI: 10.1002/chem.202402085</identifier><identifier>PMID: 38926940</identifier><language>eng</language><publisher>Germany</publisher><subject>Alkyne ; Copper catalysis ; Cyclization ; Hydroamination ; Indole-fused quinazolinone</subject><ispartof>Chemistry : a European journal, 2024-09, Vol.30 (50), p.e202402085-n/a</ispartof><rights>2024 Wiley-VCH GmbH</rights><rights>2024 Wiley‐VCH GmbH.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-c1975-cdd35f1aa941372a53a922e12a2088cb2d71a6ba45b33c1d0bd91434ab5b31a53</cites><orcidid>0000-0002-1458-5383 ; 0000-0002-4005-2249 ; 0000-0003-3128-2381 ; 0000-0003-3437-2462</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%2Fchem.202402085$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fchem.202402085$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/38926940$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Liu, Xiao‐Qing</creatorcontrib><creatorcontrib>Chen, Yan‐Jie</creatorcontrib><creatorcontrib>Zou, Pei‐Sen</creatorcontrib><creatorcontrib>Su, Jun‐Cheng</creatorcontrib><creatorcontrib>Pan, Cheng‐Xue</creatorcontrib><creatorcontrib>Mo, Dong‐Liang</creatorcontrib><creatorcontrib>Su, Gui‐Fa</creatorcontrib><title>Synthesis of Indole‐Fused Pyrazino[1,2‐a]quinazolinones by Copper(I)‐Catalyzed Selective Hydroamination‐Cyclization of Alkynyl‐tethered Quinazolinones</title><title>Chemistry : a European journal</title><addtitle>Chemistry</addtitle><description>We described a copper(I)‐catalyzed atom economic and selective hydroamination‐cyclization of alkynyl‐tethered quinazolinones to prepare a variety of indole‐fused pyrazino[1,2‐a]quinazolinones in good to excellent yields ranging from 39 %–99 % under mild reaction conditions. Control experiments revealed that coordination‐directed method of quinazolinone moiety with copper(I) was important for the selective hydroamination‐cyclization of alkynes at the N1‐atom instead of N3‐atom of quinazolinone. The reaction could be easily performed at gram scales and some prepared indole‐fused pyrazino[1,2‐a]quinazolinones with donating groups on the indole moiety showed a distinct fluorescence emission wavelength with blue shift under the acid conditions.
We described a copper(I)‐catalyzed atom‐economic and highly chemo‐selective hydroamination‐cyclization of alkynyl‐tethered quinazolinones to prepare a variety of indole‐fused pyrazino[1,2‐a]quinazolinones in good to excellent yields under mild reaction conditions.</description><subject>Alkyne</subject><subject>Copper catalysis</subject><subject>Cyclization</subject><subject>Hydroamination</subject><subject>Indole-fused quinazolinone</subject><issn>0947-6539</issn><issn>1521-3765</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2024</creationdate><recordtype>article</recordtype><recordid>eNqFkE1OwzAUhC0EoqWwZYmyBIkU_-SnXlZRSysVASqsEIqc2FENTlLiFOSsOAJH4GycBIdCEStWlufNzHv6ADhEsI8gxGfpQuR9DLEHMRz4W6CLfIxcEgb-NuhC6oVu4BPaAXtaP0AIaUDILuiQAcUB9WAXvM9NUS-EltopM2da8FKJj9e38UoL7lyZijWyKO_QKbYiu39ayYI1pbJaIbSTGCcql0tRHU9P7DxiNVOmscG5UCKt5bNwJoZXJcttrJZl0ZpMqmTz9Ws3DtWjKYyyg1rYOyobvv6zZB_sZExpcfD99sDteHQTTdzZ5fk0Gs7cFNHQd1POiZ8hxqiHSIiZTxjFWCDMLJdBmmAeIhYkzPMTQlLEYcIp8ojHEisga--B_ro3rUqtK5HFy0rmrDIxgnGLOm5RxxvUNnC0DixXSS74xv7D1hro2vAilTD_1MXRZHTxW_4JMziUVg</recordid><startdate>20240905</startdate><enddate>20240905</enddate><creator>Liu, Xiao‐Qing</creator><creator>Chen, Yan‐Jie</creator><creator>Zou, Pei‐Sen</creator><creator>Su, Jun‐Cheng</creator><creator>Pan, Cheng‐Xue</creator><creator>Mo, Dong‐Liang</creator><creator>Su, Gui‐Fa</creator><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><orcidid>https://orcid.org/0000-0002-1458-5383</orcidid><orcidid>https://orcid.org/0000-0002-4005-2249</orcidid><orcidid>https://orcid.org/0000-0003-3128-2381</orcidid><orcidid>https://orcid.org/0000-0003-3437-2462</orcidid></search><sort><creationdate>20240905</creationdate><title>Synthesis of Indole‐Fused Pyrazino[1,2‐a]quinazolinones by Copper(I)‐Catalyzed Selective Hydroamination‐Cyclization of Alkynyl‐tethered Quinazolinones</title><author>Liu, Xiao‐Qing ; Chen, Yan‐Jie ; Zou, Pei‐Sen ; Su, Jun‐Cheng ; Pan, Cheng‐Xue ; Mo, Dong‐Liang ; Su, Gui‐Fa</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c1975-cdd35f1aa941372a53a922e12a2088cb2d71a6ba45b33c1d0bd91434ab5b31a53</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2024</creationdate><topic>Alkyne</topic><topic>Copper catalysis</topic><topic>Cyclization</topic><topic>Hydroamination</topic><topic>Indole-fused quinazolinone</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Liu, Xiao‐Qing</creatorcontrib><creatorcontrib>Chen, Yan‐Jie</creatorcontrib><creatorcontrib>Zou, Pei‐Sen</creatorcontrib><creatorcontrib>Su, Jun‐Cheng</creatorcontrib><creatorcontrib>Pan, Cheng‐Xue</creatorcontrib><creatorcontrib>Mo, Dong‐Liang</creatorcontrib><creatorcontrib>Su, Gui‐Fa</creatorcontrib><collection>PubMed</collection><collection>CrossRef</collection><jtitle>Chemistry : a European journal</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Liu, Xiao‐Qing</au><au>Chen, Yan‐Jie</au><au>Zou, Pei‐Sen</au><au>Su, Jun‐Cheng</au><au>Pan, Cheng‐Xue</au><au>Mo, Dong‐Liang</au><au>Su, Gui‐Fa</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of Indole‐Fused Pyrazino[1,2‐a]quinazolinones by Copper(I)‐Catalyzed Selective Hydroamination‐Cyclization of Alkynyl‐tethered Quinazolinones</atitle><jtitle>Chemistry : a European journal</jtitle><addtitle>Chemistry</addtitle><date>2024-09-05</date><risdate>2024</risdate><volume>30</volume><issue>50</issue><spage>e202402085</spage><epage>n/a</epage><pages>e202402085-n/a</pages><issn>0947-6539</issn><eissn>1521-3765</eissn><abstract>We described a copper(I)‐catalyzed atom economic and selective hydroamination‐cyclization of alkynyl‐tethered quinazolinones to prepare a variety of indole‐fused pyrazino[1,2‐a]quinazolinones in good to excellent yields ranging from 39 %–99 % under mild reaction conditions. Control experiments revealed that coordination‐directed method of quinazolinone moiety with copper(I) was important for the selective hydroamination‐cyclization of alkynes at the N1‐atom instead of N3‐atom of quinazolinone. The reaction could be easily performed at gram scales and some prepared indole‐fused pyrazino[1,2‐a]quinazolinones with donating groups on the indole moiety showed a distinct fluorescence emission wavelength with blue shift under the acid conditions.
We described a copper(I)‐catalyzed atom‐economic and highly chemo‐selective hydroamination‐cyclization of alkynyl‐tethered quinazolinones to prepare a variety of indole‐fused pyrazino[1,2‐a]quinazolinones in good to excellent yields under mild reaction conditions.</abstract><cop>Germany</cop><pmid>38926940</pmid><doi>10.1002/chem.202402085</doi><tpages>6</tpages><orcidid>https://orcid.org/0000-0002-1458-5383</orcidid><orcidid>https://orcid.org/0000-0002-4005-2249</orcidid><orcidid>https://orcid.org/0000-0003-3128-2381</orcidid><orcidid>https://orcid.org/0000-0003-3437-2462</orcidid></addata></record> |
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| ispartof | Chemistry : a European journal, 2024-09, Vol.30 (50), p.e202402085-n/a |
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| source | Wiley Online Library Journals Frontfile Complete |
| subjects | Alkyne Copper catalysis Cyclization Hydroamination Indole-fused quinazolinone |
| title | Synthesis of Indole‐Fused Pyrazino[1,2‐a]quinazolinones by Copper(I)‐Catalyzed Selective Hydroamination‐Cyclization of Alkynyl‐tethered Quinazolinones |
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