Tandem Radical Cyclization of N-Arylacrylamides: An Emerging Platform for the Construction of 3,3-Disubstituted Oxindoles
Abstract 3,3-Disubstituted oxindoles are an important family of biologically active heterocycles, and numerous synthetic methodologies have been developed for their synthesis over past decades. Recently, the tandem radical cyclization of N -arylacrylamides has provided a new powerful approach to acc...
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| Veröffentlicht in: | Synthesis (Stuttgart) 2014-12, Vol.47 (5), p.604-629 |
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| container_title | Synthesis (Stuttgart) |
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| creator | Chen, Jia-Rong Yu, Xiao-Ye Xiao, Wen-Jing |
| description | Abstract
3,3-Disubstituted oxindoles are an important family of biologically active heterocycles, and numerous synthetic methodologies have been developed for their synthesis over past decades. Recently, the tandem radical cyclization of
N
-arylacrylamides has provided a new powerful approach to access various diversely functionalized 3,3-disubstituted oxindoles. This review will highlight recent advances in this field as well as applications in natural product synthesis in terms of different types of radical source. Particular emphases have also been placed on working models.
1 Introduction
2 Tandem Radical Addition/Cyclization Reaction of
N
-Arylacrylamides with Carbon Radicals
2.1 Aryl Radicals
2.2 Alkyl Radicals
2.3 Fluorine-Containing Carbon Radicals
2.4 Acyl Radicals
3 Tandem Radical Addition/Cyclization Reaction of
N
-Arylacrylamides with Heteroatom Radicals
3.1 Phosphonyl Radicals
3.2 Sulfur Radicals
3.3 Nitrogen Radicals
4 Conclusion and Perspective |
| doi_str_mv | 10.1055/s-0034-1378944 |
| format | Article |
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3,3-Disubstituted oxindoles are an important family of biologically active heterocycles, and numerous synthetic methodologies have been developed for their synthesis over past decades. Recently, the tandem radical cyclization of
N
-arylacrylamides has provided a new powerful approach to access various diversely functionalized 3,3-disubstituted oxindoles. This review will highlight recent advances in this field as well as applications in natural product synthesis in terms of different types of radical source. Particular emphases have also been placed on working models.
1 Introduction
2 Tandem Radical Addition/Cyclization Reaction of
N
-Arylacrylamides with Carbon Radicals
2.1 Aryl Radicals
2.2 Alkyl Radicals
2.3 Fluorine-Containing Carbon Radicals
2.4 Acyl Radicals
3 Tandem Radical Addition/Cyclization Reaction of
N
-Arylacrylamides with Heteroatom Radicals
3.1 Phosphonyl Radicals
3.2 Sulfur Radicals
3.3 Nitrogen Radicals
4 Conclusion and Perspective</description><identifier>ISSN: 0039-7881</identifier><identifier>EISSN: 1437-210X</identifier><identifier>DOI: 10.1055/s-0034-1378944</identifier><language>eng</language><publisher>Stuttgart · New York: Georg Thieme Verlag</publisher><subject>short review</subject><ispartof>Synthesis (Stuttgart), 2014-12, Vol.47 (5), p.604-629</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c413t-901538df14c16981bc62337cbb4834a51bf809cacb929be6c2ffc3d081eb6e4d3</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://www.thieme-connect.de/products/ejournals/pdf/10.1055/s-0034-1378944.pdf$$EPDF$$P50$$Gthieme$$H</linktopdf><linktohtml>$$Uhttps://www.thieme-connect.de/products/ejournals/html/10.1055/s-0034-1378944$$EHTML$$P50$$Gthieme$$H</linktohtml><link.rule.ids>314,780,784,3017,3018,27924,27925,54559,54560</link.rule.ids></links><search><creatorcontrib>Chen, Jia-Rong</creatorcontrib><creatorcontrib>Yu, Xiao-Ye</creatorcontrib><creatorcontrib>Xiao, Wen-Jing</creatorcontrib><title>Tandem Radical Cyclization of N-Arylacrylamides: An Emerging Platform for the Construction of 3,3-Disubstituted Oxindoles</title><title>Synthesis (Stuttgart)</title><addtitle>Synthesis</addtitle><description>Abstract
3,3-Disubstituted oxindoles are an important family of biologically active heterocycles, and numerous synthetic methodologies have been developed for their synthesis over past decades. Recently, the tandem radical cyclization of
N
-arylacrylamides has provided a new powerful approach to access various diversely functionalized 3,3-disubstituted oxindoles. This review will highlight recent advances in this field as well as applications in natural product synthesis in terms of different types of radical source. Particular emphases have also been placed on working models.
1 Introduction
2 Tandem Radical Addition/Cyclization Reaction of
N
-Arylacrylamides with Carbon Radicals
2.1 Aryl Radicals
2.2 Alkyl Radicals
2.3 Fluorine-Containing Carbon Radicals
2.4 Acyl Radicals
3 Tandem Radical Addition/Cyclization Reaction of
N
-Arylacrylamides with Heteroatom Radicals
3.1 Phosphonyl Radicals
3.2 Sulfur Radicals
3.3 Nitrogen Radicals
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3,3-Disubstituted oxindoles are an important family of biologically active heterocycles, and numerous synthetic methodologies have been developed for their synthesis over past decades. Recently, the tandem radical cyclization of
N
-arylacrylamides has provided a new powerful approach to access various diversely functionalized 3,3-disubstituted oxindoles. This review will highlight recent advances in this field as well as applications in natural product synthesis in terms of different types of radical source. Particular emphases have also been placed on working models.
1 Introduction
2 Tandem Radical Addition/Cyclization Reaction of
N
-Arylacrylamides with Carbon Radicals
2.1 Aryl Radicals
2.2 Alkyl Radicals
2.3 Fluorine-Containing Carbon Radicals
2.4 Acyl Radicals
3 Tandem Radical Addition/Cyclization Reaction of
N
-Arylacrylamides with Heteroatom Radicals
3.1 Phosphonyl Radicals
3.2 Sulfur Radicals
3.3 Nitrogen Radicals
4 Conclusion and Perspective</abstract><cop>Stuttgart · New York</cop><pub>Georg Thieme Verlag</pub><doi>10.1055/s-0034-1378944</doi><tpages>26</tpages></addata></record> |
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| issn | 0039-7881 1437-210X |
| language | eng |
| recordid | cdi_crossref_primary_10_1055_s_0034_1378944 |
| source | Thieme Connect Journals |
| subjects | short review |
| title | Tandem Radical Cyclization of N-Arylacrylamides: An Emerging Platform for the Construction of 3,3-Disubstituted Oxindoles |
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