Silver(I) Triflate‐Catalyzed Protocol for the Post‐Ugi Synthesis of Spiroindolines
A silver(I) triflate‐catalyzed protocol for the post‐Ugi synthesis of tetracyclic spiroindolines has been developed. The protocol worked best for indole‐3‐carbaldehyde‐derived Ugi adducts obtained using anilines and 3‐aryl propiolic acids. Thus, it is complementary to the previous cationic gold‐cata...
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| Veröffentlicht in: | Advanced synthesis & catalysis 2020-01, Vol.362 (1), p.261-268 |
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| container_title | Advanced synthesis & catalysis |
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| creator | Zaman, Manzoor Hasan, Muhammad Peshkov, Anatoly A. Van Hecke, Kristof Van der Eycken, Erik V. Pereshivko, Olga P. Peshkov, Vsevolod A. |
| description | A silver(I) triflate‐catalyzed protocol for the post‐Ugi synthesis of tetracyclic spiroindolines has been developed. The protocol worked best for indole‐3‐carbaldehyde‐derived Ugi adducts obtained using anilines and 3‐aryl propiolic acids. Thus, it is complementary to the previous cationic gold‐catalyzed procedure that was developed for analogues Ugi substrates derived from aliphatic amines and 3‐alkyl propiolic acids. Furthermore, we have demonstrated that under our new settings this domino Friedel‐Crafts ipso cyclization / imine trapping process could be efficiently combined with the preceding four‐component Ugi reaction into a two‐step one‐pot transformation. |
| doi_str_mv | 10.1002/adsc.201901064 |
| format | Article |
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The protocol worked best for indole‐3‐carbaldehyde‐derived Ugi adducts obtained using anilines and 3‐aryl propiolic acids. Thus, it is complementary to the previous cationic gold‐catalyzed procedure that was developed for analogues Ugi substrates derived from aliphatic amines and 3‐alkyl propiolic acids. Furthermore, we have demonstrated that under our new settings this domino Friedel‐Crafts ipso cyclization / imine trapping process could be efficiently combined with the preceding four‐component Ugi reaction into a two‐step one‐pot transformation.</description><identifier>ISSN: 1615-4150</identifier><identifier>EISSN: 1615-4169</identifier><identifier>DOI: 10.1002/adsc.201901064</identifier><language>eng</language><publisher>Heidelberg: Wiley Subscription Services, Inc</publisher><subject>Adducts ; Aliphatic amines ; Aniline ; Aromatic compounds ; Domino reactions ; Multicomponent reactions ; Nitrogen heterocycles ; Silver catalysis ; Spiro compounds ; Substrates</subject><ispartof>Advanced synthesis & catalysis, 2020-01, Vol.362 (1), p.261-268</ispartof><rights>2020 Wiley‐VCH Verlag GmbH & Co. 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The protocol worked best for indole‐3‐carbaldehyde‐derived Ugi adducts obtained using anilines and 3‐aryl propiolic acids. Thus, it is complementary to the previous cationic gold‐catalyzed procedure that was developed for analogues Ugi substrates derived from aliphatic amines and 3‐alkyl propiolic acids. Furthermore, we have demonstrated that under our new settings this domino Friedel‐Crafts ipso cyclization / imine trapping process could be efficiently combined with the preceding four‐component Ugi reaction into a two‐step one‐pot transformation.</description><subject>Adducts</subject><subject>Aliphatic amines</subject><subject>Aniline</subject><subject>Aromatic compounds</subject><subject>Domino reactions</subject><subject>Multicomponent reactions</subject><subject>Nitrogen heterocycles</subject><subject>Silver catalysis</subject><subject>Spiro compounds</subject><subject>Substrates</subject><issn>1615-4150</issn><issn>1615-4169</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><recordid>eNqFkL9OwzAQhy0EEqWwMltigSHFjp3EHqvwr1IlKqVltRzHBlchLnZaFCYegWfkSUhVVEamO52-393pA-AcoxFGKL6WVVCjGGGOMErpARjgFCcRxSk_3PcJOgYnISwRwhnLsgF4Kmy90f5ycgXn3ppatvr78yuXray7D13BmXetU66GxnnYvmg4c6HticWzhUXX9JNgA3QGFivrnW0qV9tGh1NwZGQd9NlvHYLF3e08f4imj_eTfDyNFOGURqz_VWOilaFcxkzxjKaKM00NJSzWJSElo9pUXDGCdRajUmGCFFNVKcskJWQILnZ7V969rXVoxdKtfdOfFDEhNE0yFKc9NdpRyrsQvDZi5e2r9J3ASGzdia07sXfXB_gu8G5r3f1Di_FNkf9lfwCqv3Tv</recordid><startdate>20200107</startdate><enddate>20200107</enddate><creator>Zaman, Manzoor</creator><creator>Hasan, Muhammad</creator><creator>Peshkov, Anatoly A.</creator><creator>Van Hecke, Kristof</creator><creator>Van der Eycken, Erik V.</creator><creator>Pereshivko, Olga P.</creator><creator>Peshkov, Vsevolod A.</creator><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7U5</scope><scope>8FD</scope><scope>L7M</scope></search><sort><creationdate>20200107</creationdate><title>Silver(I) Triflate‐Catalyzed Protocol for the Post‐Ugi Synthesis of Spiroindolines</title><author>Zaman, Manzoor ; Hasan, Muhammad ; Peshkov, Anatoly A. ; Van Hecke, Kristof ; Van der Eycken, Erik V. ; Pereshivko, Olga P. ; Peshkov, Vsevolod A.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3944-8901e13ecf49a28c9746c98e4f4382eb33b84efd9c831e720bc130c8cdbab5633</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Adducts</topic><topic>Aliphatic amines</topic><topic>Aniline</topic><topic>Aromatic compounds</topic><topic>Domino reactions</topic><topic>Multicomponent reactions</topic><topic>Nitrogen heterocycles</topic><topic>Silver catalysis</topic><topic>Spiro compounds</topic><topic>Substrates</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Zaman, Manzoor</creatorcontrib><creatorcontrib>Hasan, Muhammad</creatorcontrib><creatorcontrib>Peshkov, Anatoly A.</creatorcontrib><creatorcontrib>Van Hecke, Kristof</creatorcontrib><creatorcontrib>Van der Eycken, Erik V.</creatorcontrib><creatorcontrib>Pereshivko, Olga P.</creatorcontrib><creatorcontrib>Peshkov, Vsevolod A.</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>Zaman, Manzoor</au><au>Hasan, Muhammad</au><au>Peshkov, Anatoly A.</au><au>Van Hecke, Kristof</au><au>Van der Eycken, Erik V.</au><au>Pereshivko, Olga P.</au><au>Peshkov, Vsevolod A.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Silver(I) Triflate‐Catalyzed Protocol for the Post‐Ugi Synthesis of Spiroindolines</atitle><jtitle>Advanced synthesis & catalysis</jtitle><date>2020-01-07</date><risdate>2020</risdate><volume>362</volume><issue>1</issue><spage>261</spage><epage>268</epage><pages>261-268</pages><issn>1615-4150</issn><eissn>1615-4169</eissn><abstract>A silver(I) triflate‐catalyzed protocol for the post‐Ugi synthesis of tetracyclic spiroindolines has been developed. The protocol worked best for indole‐3‐carbaldehyde‐derived Ugi adducts obtained using anilines and 3‐aryl propiolic acids. Thus, it is complementary to the previous cationic gold‐catalyzed procedure that was developed for analogues Ugi substrates derived from aliphatic amines and 3‐alkyl propiolic acids. Furthermore, we have demonstrated that under our new settings this domino Friedel‐Crafts ipso cyclization / imine trapping process could be efficiently combined with the preceding four‐component Ugi reaction into a two‐step one‐pot transformation.</abstract><cop>Heidelberg</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/adsc.201901064</doi><tpages>8</tpages><oa>free_for_read</oa></addata></record> |
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| subjects | Adducts Aliphatic amines Aniline Aromatic compounds Domino reactions Multicomponent reactions Nitrogen heterocycles Silver catalysis Spiro compounds Substrates |
| title | Silver(I) Triflate‐Catalyzed Protocol for the Post‐Ugi Synthesis of Spiroindolines |
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