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One‐Pot Synthesis of Polysubstituted Pyrroles via Sequential Ketenimine Formation/Ag(I)‐Catalyzed Alkyne Cycloisomerisation Starting from Ylide Adducts
Main observation and conclusion A simple one pot synthesis of polysubstituted pyrroles via ketenimine formation/Ag(I)‐catalyzed alkyne cycloisomerisation has been developed. The easily accessible phosphorane ylide derivatives reacted with isocyanates, producing highly active ketenimines that were th...
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| Published in: | Chinese journal of chemistry 2021-06, Vol.39 (6), p.1553-1557 |
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| Main Authors: | , , , , , , , , |
| Format: | Article |
| Language: | English |
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| cited_by | cdi_FETCH-LOGICAL-c3549-3eda3d6e32665bed00521d1744ea950364139b35c30dd0cfa2326290969f4d573 |
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| cites | cdi_FETCH-LOGICAL-c3549-3eda3d6e32665bed00521d1744ea950364139b35c30dd0cfa2326290969f4d573 |
| container_end_page | 1557 |
| container_issue | 6 |
| container_start_page | 1553 |
| container_title | Chinese journal of chemistry |
| container_volume | 39 |
| creator | Xiong, Jun Mu, Zhi‐Ying Yao, Gang Zhang, Jia‐An Feng, Qi‐Xun He, Hui‐Ting Pang, Yong‐Long Shi, Hang Ding, Ming‐Wu |
| description | Main observation and conclusion
A simple one pot synthesis of polysubstituted pyrroles via ketenimine formation/Ag(I)‐catalyzed alkyne cycloisomerisation has been developed. The easily accessible phosphorane ylide derivatives reacted with isocyanates, producing highly active ketenimines that were then treated with amines, which afforded substituted pyrroles by a 5‐exo‐dig cyclization/isomerization in the presence of a Ag(I) catalyst in good overall yields.
We developed an efficient one‐pot method for the preparation of polysubstituted pyrroles via ketenimine formation/Ag(I)‐catalyzed alkyne cycloisomerisation starting from the easily accessible phosphorane ylide derivatives under mild reaction conditions. |
| doi_str_mv | 10.1002/cjoc.202000639 |
| format | article |
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A simple one pot synthesis of polysubstituted pyrroles via ketenimine formation/Ag(I)‐catalyzed alkyne cycloisomerisation has been developed. The easily accessible phosphorane ylide derivatives reacted with isocyanates, producing highly active ketenimines that were then treated with amines, which afforded substituted pyrroles by a 5‐exo‐dig cyclization/isomerization in the presence of a Ag(I) catalyst in good overall yields.
We developed an efficient one‐pot method for the preparation of polysubstituted pyrroles via ketenimine formation/Ag(I)‐catalyzed alkyne cycloisomerisation starting from the easily accessible phosphorane ylide derivatives under mild reaction conditions.</description><identifier>ISSN: 1001-604X</identifier><identifier>EISSN: 1614-7065</identifier><identifier>DOI: 10.1002/cjoc.202000639</identifier><language>eng</language><publisher>Weinheim: WILEY‐VCH Verlag GmbH & Co. KGaA</publisher><subject>Adducts ; Ag(I)‐catalysed ; Alkynes ; Amines ; Catalysts ; Cyclic compounds ; Isocyanates ; Isomerization ; Ketenimine ; One‐pot ; Pyrrolel ; Pyrroles ; Ylide</subject><ispartof>Chinese journal of chemistry, 2021-06, Vol.39 (6), p.1553-1557</ispartof><rights>2021 SIOC, CAS, Shanghai and Wiley‐VCH GmbH</rights><rights>2021 SIOC, CAS, Shanghai, & WILEY‐VCH GmbH</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3549-3eda3d6e32665bed00521d1744ea950364139b35c30dd0cfa2326290969f4d573</citedby><cites>FETCH-LOGICAL-c3549-3eda3d6e32665bed00521d1744ea950364139b35c30dd0cfa2326290969f4d573</cites></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>Xiong, Jun</creatorcontrib><creatorcontrib>Mu, Zhi‐Ying</creatorcontrib><creatorcontrib>Yao, Gang</creatorcontrib><creatorcontrib>Zhang, Jia‐An</creatorcontrib><creatorcontrib>Feng, Qi‐Xun</creatorcontrib><creatorcontrib>He, Hui‐Ting</creatorcontrib><creatorcontrib>Pang, Yong‐Long</creatorcontrib><creatorcontrib>Shi, Hang</creatorcontrib><creatorcontrib>Ding, Ming‐Wu</creatorcontrib><title>One‐Pot Synthesis of Polysubstituted Pyrroles via Sequential Ketenimine Formation/Ag(I)‐Catalyzed Alkyne Cycloisomerisation Starting from Ylide Adducts</title><title>Chinese journal of chemistry</title><description>Main observation and conclusion
A simple one pot synthesis of polysubstituted pyrroles via ketenimine formation/Ag(I)‐catalyzed alkyne cycloisomerisation has been developed. The easily accessible phosphorane ylide derivatives reacted with isocyanates, producing highly active ketenimines that were then treated with amines, which afforded substituted pyrroles by a 5‐exo‐dig cyclization/isomerization in the presence of a Ag(I) catalyst in good overall yields.
We developed an efficient one‐pot method for the preparation of polysubstituted pyrroles via ketenimine formation/Ag(I)‐catalyzed alkyne cycloisomerisation starting from the easily accessible phosphorane ylide derivatives under mild reaction conditions.</description><subject>Adducts</subject><subject>Ag(I)‐catalysed</subject><subject>Alkynes</subject><subject>Amines</subject><subject>Catalysts</subject><subject>Cyclic compounds</subject><subject>Isocyanates</subject><subject>Isomerization</subject><subject>Ketenimine</subject><subject>One‐pot</subject><subject>Pyrrolel</subject><subject>Pyrroles</subject><subject>Ylide</subject><issn>1001-604X</issn><issn>1614-7065</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2021</creationdate><recordtype>article</recordtype><recordid>eNqFkcFu1DAQhiNEJUrLlbMlLnDIdmwnjnyMIhYKlXalLRKcIm88KV6ceLEdUDjxCL337fokdbuoHHuaOXzfPxr9WfaawoICsLNu57oFAwYAgstn2TEVtMgrEOXztAPQXEDx9UX2MoRd4quKiePsZjXi7d_rtYtkM4_xOwYTiOvJ2tk5TNsQTZwiarKevXcWA_llFNngzwnHaJQlnzHiaAYzIlk6P6ho3HhWX709f5dSGxWVnf8kvbY_5oQ0c2edCW5Ab8IDSzZR-WjGK9J7N5Bv1mgktdZTF8NpdtQrG_DVv3mSfVm-v2w-5herD-dNfZF3vCxkzlErrgVyJkS5RQ1QMqppVRSoZAlcFJTLLS87DlpD1yuWSCZBCtkXuqz4SfbmkLv3Lj0WYrtzkx_TyZaVTFaMVoIlanGgOu9C8Ni3e28G5eeWQntfQHtfQPtYQBLkQfhtLM5P0G3zadX8d-8AeJaOjw</recordid><startdate>202106</startdate><enddate>202106</enddate><creator>Xiong, Jun</creator><creator>Mu, Zhi‐Ying</creator><creator>Yao, Gang</creator><creator>Zhang, Jia‐An</creator><creator>Feng, Qi‐Xun</creator><creator>He, Hui‐Ting</creator><creator>Pang, Yong‐Long</creator><creator>Shi, Hang</creator><creator>Ding, Ming‐Wu</creator><general>WILEY‐VCH Verlag GmbH & Co. KGaA</general><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>202106</creationdate><title>One‐Pot Synthesis of Polysubstituted Pyrroles via Sequential Ketenimine Formation/Ag(I)‐Catalyzed Alkyne Cycloisomerisation Starting from Ylide Adducts</title><author>Xiong, Jun ; Mu, Zhi‐Ying ; Yao, Gang ; Zhang, Jia‐An ; Feng, Qi‐Xun ; He, Hui‐Ting ; Pang, Yong‐Long ; Shi, Hang ; Ding, Ming‐Wu</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3549-3eda3d6e32665bed00521d1744ea950364139b35c30dd0cfa2326290969f4d573</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2021</creationdate><topic>Adducts</topic><topic>Ag(I)‐catalysed</topic><topic>Alkynes</topic><topic>Amines</topic><topic>Catalysts</topic><topic>Cyclic compounds</topic><topic>Isocyanates</topic><topic>Isomerization</topic><topic>Ketenimine</topic><topic>One‐pot</topic><topic>Pyrrolel</topic><topic>Pyrroles</topic><topic>Ylide</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Xiong, Jun</creatorcontrib><creatorcontrib>Mu, Zhi‐Ying</creatorcontrib><creatorcontrib>Yao, Gang</creatorcontrib><creatorcontrib>Zhang, Jia‐An</creatorcontrib><creatorcontrib>Feng, Qi‐Xun</creatorcontrib><creatorcontrib>He, Hui‐Ting</creatorcontrib><creatorcontrib>Pang, Yong‐Long</creatorcontrib><creatorcontrib>Shi, Hang</creatorcontrib><creatorcontrib>Ding, Ming‐Wu</creatorcontrib><collection>CrossRef</collection><jtitle>Chinese journal of chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Xiong, Jun</au><au>Mu, Zhi‐Ying</au><au>Yao, Gang</au><au>Zhang, Jia‐An</au><au>Feng, Qi‐Xun</au><au>He, Hui‐Ting</au><au>Pang, Yong‐Long</au><au>Shi, Hang</au><au>Ding, Ming‐Wu</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>One‐Pot Synthesis of Polysubstituted Pyrroles via Sequential Ketenimine Formation/Ag(I)‐Catalyzed Alkyne Cycloisomerisation Starting from Ylide Adducts</atitle><jtitle>Chinese journal of chemistry</jtitle><date>2021-06</date><risdate>2021</risdate><volume>39</volume><issue>6</issue><spage>1553</spage><epage>1557</epage><pages>1553-1557</pages><issn>1001-604X</issn><eissn>1614-7065</eissn><abstract>Main observation and conclusion
A simple one pot synthesis of polysubstituted pyrroles via ketenimine formation/Ag(I)‐catalyzed alkyne cycloisomerisation has been developed. The easily accessible phosphorane ylide derivatives reacted with isocyanates, producing highly active ketenimines that were then treated with amines, which afforded substituted pyrroles by a 5‐exo‐dig cyclization/isomerization in the presence of a Ag(I) catalyst in good overall yields.
We developed an efficient one‐pot method for the preparation of polysubstituted pyrroles via ketenimine formation/Ag(I)‐catalyzed alkyne cycloisomerisation starting from the easily accessible phosphorane ylide derivatives under mild reaction conditions.</abstract><cop>Weinheim</cop><pub>WILEY‐VCH Verlag GmbH & Co. KGaA</pub><doi>10.1002/cjoc.202000639</doi><tpages>5</tpages></addata></record> |
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| ispartof | Chinese journal of chemistry, 2021-06, Vol.39 (6), p.1553-1557 |
| issn | 1001-604X 1614-7065 |
| language | eng |
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| source | Wiley-Blackwell Read & Publish Collection |
| subjects | Adducts Ag(I)‐catalysed Alkynes Amines Catalysts Cyclic compounds Isocyanates Isomerization Ketenimine One‐pot Pyrrolel Pyrroles Ylide |
| title | One‐Pot Synthesis of Polysubstituted Pyrroles via Sequential Ketenimine Formation/Ag(I)‐Catalyzed Alkyne Cycloisomerisation Starting from Ylide Adducts |
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