Boron Trifluoride Catalyzed Divergent Synthesis of 3‐Alkenyl‐3‐amino‐2‐oxindoles and Spiro‐indeneindolones from Propargylic Alcohols
An expedient method was demonstrated for the synthesis of 3‐alkenyl‐3‐amino‐2‐oxindoles from readily available propargylic alcohols and isatin imines in the presence of BF3 ⋅ Et2O as a catalyst under open‐air atmosphere. The above reaction was time‐dependent and further extended to the one‐pot synth...
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| Veröffentlicht in: | Advanced synthesis & catalysis 2019-02, Vol.361 (4), p.702-707 |
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| container_title | Advanced synthesis & catalysis |
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| creator | Muthusamy, Sengodagounder Balasubramani, Alagesan Suresh, Eringathodi |
| description | An expedient method was demonstrated for the synthesis of 3‐alkenyl‐3‐amino‐2‐oxindoles from readily available propargylic alcohols and isatin imines in the presence of BF3 ⋅ Et2O as a catalyst under open‐air atmosphere. The above reaction was time‐dependent and further extended to the one‐pot synthesis of highly substituted spiro‐indeneindolones via 1,3‐amino group migration/Friedel‐Crafts cyclization. This methodology, which tolerates a broad variety of functional groups, offers versatile and atom‐economical access to 3‐alkenyl‐3‐amino‐2‐oxindole or spiro‐indeneindolone derivatives in good yield at room temperature. |
| doi_str_mv | 10.1002/adsc.201801106 |
| format | Article |
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The above reaction was time‐dependent and further extended to the one‐pot synthesis of highly substituted spiro‐indeneindolones via 1,3‐amino group migration/Friedel‐Crafts cyclization. This methodology, which tolerates a broad variety of functional groups, offers versatile and atom‐economical access to 3‐alkenyl‐3‐amino‐2‐oxindole or spiro‐indeneindolone derivatives in good yield at room temperature.</description><identifier>ISSN: 1615-4150</identifier><identifier>EISSN: 1615-4169</identifier><identifier>DOI: 10.1002/adsc.201801106</identifier><language>eng</language><publisher>Heidelberg: Wiley Subscription Services, Inc</publisher><subject>3-alkenyl-3-amino-2-oxindoles ; Alcohol ; Alcohols ; Boron ; boron trifluoride catalyst ; Chemical synthesis ; Functional groups ; Imines ; isatin imines ; Migration ; propargylic alcohols ; spiro-indeneindolones ; Time dependence</subject><ispartof>Advanced synthesis & catalysis, 2019-02, Vol.361 (4), p.702-707</ispartof><rights>2019 Wiley‐VCH Verlag GmbH & Co. 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The above reaction was time‐dependent and further extended to the one‐pot synthesis of highly substituted spiro‐indeneindolones via 1,3‐amino group migration/Friedel‐Crafts cyclization. This methodology, which tolerates a broad variety of functional groups, offers versatile and atom‐economical access to 3‐alkenyl‐3‐amino‐2‐oxindole or spiro‐indeneindolone derivatives in good yield at room temperature.</description><subject>3-alkenyl-3-amino-2-oxindoles</subject><subject>Alcohol</subject><subject>Alcohols</subject><subject>Boron</subject><subject>boron trifluoride catalyst</subject><subject>Chemical synthesis</subject><subject>Functional groups</subject><subject>Imines</subject><subject>isatin imines</subject><subject>Migration</subject><subject>propargylic alcohols</subject><subject>spiro-indeneindolones</subject><subject>Time dependence</subject><issn>1615-4150</issn><issn>1615-4169</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2019</creationdate><recordtype>article</recordtype><recordid>eNqFUMtOwzAQjBBIPK-cLXFu2Y0bOzmW8pSQQCqcIxOvweDaxW6BcOIT-o18CSlFcOSwmt2dmV1psmwfoY8A-aHSqenngCUggljLtlBg0RugqNZ_-wI2s-2UHgFQllJuZYujEINnN9EaNw_RamIjNVOufSfNju0LxXvyMzZu_eyBkk0sGMY_PxZD90S-dV23nNTE-tBh3lV4s14HR4kpr9l4auOS6Xbk6ZsJvuNMDBN2HcNUxfvW2YYNXRMegku72YZRLtHeD-5kt6cnN6Pz3uXV2cVoeNlrOErRyzVwpRRqkqqSeiBMjiS4VhXwAkBqKA3lShkcFFwKVeXG0F0BUqApBXG-kx2s7k5jeJ5TmtWPYR5997LOseRYcChFp-qvVE0MKUUy9TTaiYptjVAvU6-Xqde_qXeGamV4tY7af9T18Hg8-vN-ASXAjto</recordid><startdate>20190219</startdate><enddate>20190219</enddate><creator>Muthusamy, Sengodagounder</creator><creator>Balasubramani, Alagesan</creator><creator>Suresh, Eringathodi</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>20190219</creationdate><title>Boron Trifluoride Catalyzed Divergent Synthesis of 3‐Alkenyl‐3‐amino‐2‐oxindoles and Spiro‐indeneindolones from Propargylic Alcohols</title><author>Muthusamy, Sengodagounder ; Balasubramani, Alagesan ; Suresh, Eringathodi</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3176-2d03aaa1de7a97d46f21e63da9035007d08fe2aaf145376a92ffeb50761f86e33</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2019</creationdate><topic>3-alkenyl-3-amino-2-oxindoles</topic><topic>Alcohol</topic><topic>Alcohols</topic><topic>Boron</topic><topic>boron trifluoride catalyst</topic><topic>Chemical synthesis</topic><topic>Functional groups</topic><topic>Imines</topic><topic>isatin imines</topic><topic>Migration</topic><topic>propargylic alcohols</topic><topic>spiro-indeneindolones</topic><topic>Time dependence</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Muthusamy, Sengodagounder</creatorcontrib><creatorcontrib>Balasubramani, Alagesan</creatorcontrib><creatorcontrib>Suresh, Eringathodi</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>Muthusamy, Sengodagounder</au><au>Balasubramani, Alagesan</au><au>Suresh, Eringathodi</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Boron Trifluoride Catalyzed Divergent Synthesis of 3‐Alkenyl‐3‐amino‐2‐oxindoles and Spiro‐indeneindolones from Propargylic Alcohols</atitle><jtitle>Advanced synthesis & catalysis</jtitle><date>2019-02-19</date><risdate>2019</risdate><volume>361</volume><issue>4</issue><spage>702</spage><epage>707</epage><pages>702-707</pages><issn>1615-4150</issn><eissn>1615-4169</eissn><abstract>An expedient method was demonstrated for the synthesis of 3‐alkenyl‐3‐amino‐2‐oxindoles from readily available propargylic alcohols and isatin imines in the presence of BF3 ⋅ Et2O as a catalyst under open‐air atmosphere. 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| ispartof | Advanced synthesis & catalysis, 2019-02, Vol.361 (4), p.702-707 |
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| source | Wiley Online Library Journals Frontfile Complete |
| subjects | 3-alkenyl-3-amino-2-oxindoles Alcohol Alcohols Boron boron trifluoride catalyst Chemical synthesis Functional groups Imines isatin imines Migration propargylic alcohols spiro-indeneindolones Time dependence |
| title | Boron Trifluoride Catalyzed Divergent Synthesis of 3‐Alkenyl‐3‐amino‐2‐oxindoles and Spiro‐indeneindolones from Propargylic Alcohols |
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