Selectfluor‐Mediated Synthesis of Fluoro Spiro 3(2H)‐Furanone Derivatives via Domino Fluorination–Defluorination
An unprecedented Domino transformation towards diverse fluorinated spiro benzothiazinyl furanone scaffolds has been developed from 1,3‐diketone embedded benzothiazines and Selectfluor through fluorinative intramolecular cyclization. The transformation is triggered by fluorine insertion to form a dif...
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| Veröffentlicht in: | European journal of organic chemistry 2018-01, Vol.2018 (3), p.413-417 |
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| container_title | European journal of organic chemistry |
| container_volume | 2018 |
| creator | Krishna Swaroop, Desireddy Ravi Kumar, Nagiri Nagender, Punna Jitender Dev, Gaddameedi Jagadeesh Babu, Nanubolu Narsaiah, Banda |
| description | An unprecedented Domino transformation towards diverse fluorinated spiro benzothiazinyl furanone scaffolds has been developed from 1,3‐diketone embedded benzothiazines and Selectfluor through fluorinative intramolecular cyclization. The transformation is triggered by fluorine insertion to form a difluoro intermediate, which is responsible for the formation of fluorinated spiro 3(2H)‐furanone derivatives. We have also succeeded to synthesize non‐fluorinated spiro 3(2H)‐furanone derivatives by oxidative cyclization using AgF.
A series of novel fluorinated spiro 3(2H)‐furanone derivatives were prepared from benzothiazines through Domino fluorinative intramolecular cyclization using Selectfluor under mild conditions. It involves fluorine insertion followed by spiroannulation. Non fluorinated spiro 3(2H)‐furanone derivatives also accomplished by AgF mediated oxidative cyclization. |
| doi_str_mv | 10.1002/ejoc.201701668 |
| format | Article |
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A series of novel fluorinated spiro 3(2H)‐furanone derivatives were prepared from benzothiazines through Domino fluorinative intramolecular cyclization using Selectfluor under mild conditions. It involves fluorine insertion followed by spiroannulation. Non fluorinated spiro 3(2H)‐furanone derivatives also accomplished by AgF mediated oxidative cyclization.</description><identifier>ISSN: 1434-193X</identifier><identifier>EISSN: 1099-0690</identifier><identifier>DOI: 10.1002/ejoc.201701668</identifier><language>eng</language><publisher>Weinheim: Wiley Subscription Services, Inc</publisher><subject>Benzothiazine ; Defluorination ; Derivatives ; Domino reactions ; Fluorinated compounds ; Fluorination ; Fluorine ; Furanone synthesis ; Scaffolds ; Spiro annulation ; Transformations</subject><ispartof>European journal of organic chemistry, 2018-01, Vol.2018 (3), p.413-417</ispartof><rights>2018 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2018 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3178-f9b5e6b519c534a8bdb51e99d4e81fcff7d51c675b6ebd968063cc9d7415eaea3</citedby><cites>FETCH-LOGICAL-c3178-f9b5e6b519c534a8bdb51e99d4e81fcff7d51c675b6ebd968063cc9d7415eaea3</cites><orcidid>0000-0001-9409-3604</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%2Fejoc.201701668$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fejoc.201701668$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids></links><search><creatorcontrib>Krishna Swaroop, Desireddy</creatorcontrib><creatorcontrib>Ravi Kumar, Nagiri</creatorcontrib><creatorcontrib>Nagender, Punna</creatorcontrib><creatorcontrib>Jitender Dev, Gaddameedi</creatorcontrib><creatorcontrib>Jagadeesh Babu, Nanubolu</creatorcontrib><creatorcontrib>Narsaiah, Banda</creatorcontrib><title>Selectfluor‐Mediated Synthesis of Fluoro Spiro 3(2H)‐Furanone Derivatives via Domino Fluorination–Defluorination</title><title>European journal of organic chemistry</title><description>An unprecedented Domino transformation towards diverse fluorinated spiro benzothiazinyl furanone scaffolds has been developed from 1,3‐diketone embedded benzothiazines and Selectfluor through fluorinative intramolecular cyclization. The transformation is triggered by fluorine insertion to form a difluoro intermediate, which is responsible for the formation of fluorinated spiro 3(2H)‐furanone derivatives. We have also succeeded to synthesize non‐fluorinated spiro 3(2H)‐furanone derivatives by oxidative cyclization using AgF.
A series of novel fluorinated spiro 3(2H)‐furanone derivatives were prepared from benzothiazines through Domino fluorinative intramolecular cyclization using Selectfluor under mild conditions. It involves fluorine insertion followed by spiroannulation. Non fluorinated spiro 3(2H)‐furanone derivatives also accomplished by AgF mediated oxidative cyclization.</description><subject>Benzothiazine</subject><subject>Defluorination</subject><subject>Derivatives</subject><subject>Domino reactions</subject><subject>Fluorinated compounds</subject><subject>Fluorination</subject><subject>Fluorine</subject><subject>Furanone synthesis</subject><subject>Scaffolds</subject><subject>Spiro annulation</subject><subject>Transformations</subject><issn>1434-193X</issn><issn>1099-0690</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2018</creationdate><recordtype>article</recordtype><recordid>eNqFkL9OwzAQxiMEEqWwMkdigSHFrhMnHlH_UFBRh4LEZjnOWbgKcbGToG59BCTesE-CqyBgY7k73ff97qQvCM4xGmCEhtewMnIwRDhFmNLsIOhhxFiEKEOHfo5JHGFGno-DE-dWCCFGKe4F7RJKkLUqG2N3248HKLSooQiXm6p-AaddaFQ43asmXK61r-RyOLvy1mljRWUqCMdgdStq3YILWy3CsXnVlekgXXnBVLvt5xjUn8VpcKRE6eDsu_eDp-nkcTSL5ovbu9HNPJIEp1mkWJ4AzRPMZEJikeWFn4GxIoYMK6lUWiRY0jTJKeQFoxmiREpWpDFOQIAg_eCiu7u25q0BV_OVaWzlX3LMMpbFKYuJdw06l7TGOQuKr61-FXbDMeL7bPk-W_6TrQdYB7zrEjb_uPnkfjH6Zb8ALmiDVQ</recordid><startdate>20180123</startdate><enddate>20180123</enddate><creator>Krishna Swaroop, Desireddy</creator><creator>Ravi Kumar, Nagiri</creator><creator>Nagender, Punna</creator><creator>Jitender Dev, Gaddameedi</creator><creator>Jagadeesh Babu, Nanubolu</creator><creator>Narsaiah, Banda</creator><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope><orcidid>https://orcid.org/0000-0001-9409-3604</orcidid></search><sort><creationdate>20180123</creationdate><title>Selectfluor‐Mediated Synthesis of Fluoro Spiro 3(2H)‐Furanone Derivatives via Domino Fluorination–Defluorination</title><author>Krishna Swaroop, Desireddy ; Ravi Kumar, Nagiri ; Nagender, Punna ; Jitender Dev, Gaddameedi ; Jagadeesh Babu, Nanubolu ; Narsaiah, Banda</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3178-f9b5e6b519c534a8bdb51e99d4e81fcff7d51c675b6ebd968063cc9d7415eaea3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2018</creationdate><topic>Benzothiazine</topic><topic>Defluorination</topic><topic>Derivatives</topic><topic>Domino reactions</topic><topic>Fluorinated compounds</topic><topic>Fluorination</topic><topic>Fluorine</topic><topic>Furanone synthesis</topic><topic>Scaffolds</topic><topic>Spiro annulation</topic><topic>Transformations</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Krishna Swaroop, Desireddy</creatorcontrib><creatorcontrib>Ravi Kumar, Nagiri</creatorcontrib><creatorcontrib>Nagender, Punna</creatorcontrib><creatorcontrib>Jitender Dev, Gaddameedi</creatorcontrib><creatorcontrib>Jagadeesh Babu, Nanubolu</creatorcontrib><creatorcontrib>Narsaiah, Banda</creatorcontrib><collection>CrossRef</collection><jtitle>European journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Krishna Swaroop, Desireddy</au><au>Ravi Kumar, Nagiri</au><au>Nagender, Punna</au><au>Jitender Dev, Gaddameedi</au><au>Jagadeesh Babu, Nanubolu</au><au>Narsaiah, Banda</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Selectfluor‐Mediated Synthesis of Fluoro Spiro 3(2H)‐Furanone Derivatives via Domino Fluorination–Defluorination</atitle><jtitle>European journal of organic chemistry</jtitle><date>2018-01-23</date><risdate>2018</risdate><volume>2018</volume><issue>3</issue><spage>413</spage><epage>417</epage><pages>413-417</pages><issn>1434-193X</issn><eissn>1099-0690</eissn><abstract>An unprecedented Domino transformation towards diverse fluorinated spiro benzothiazinyl furanone scaffolds has been developed from 1,3‐diketone embedded benzothiazines and Selectfluor through fluorinative intramolecular cyclization. The transformation is triggered by fluorine insertion to form a difluoro intermediate, which is responsible for the formation of fluorinated spiro 3(2H)‐furanone derivatives. We have also succeeded to synthesize non‐fluorinated spiro 3(2H)‐furanone derivatives by oxidative cyclization using AgF.
A series of novel fluorinated spiro 3(2H)‐furanone derivatives were prepared from benzothiazines through Domino fluorinative intramolecular cyclization using Selectfluor under mild conditions. It involves fluorine insertion followed by spiroannulation. Non fluorinated spiro 3(2H)‐furanone derivatives also accomplished by AgF mediated oxidative cyclization.</abstract><cop>Weinheim</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/ejoc.201701668</doi><tpages>5</tpages><orcidid>https://orcid.org/0000-0001-9409-3604</orcidid></addata></record> |
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| ispartof | European journal of organic chemistry, 2018-01, Vol.2018 (3), p.413-417 |
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| language | eng |
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| source | Wiley Online Library Journals Frontfile Complete |
| subjects | Benzothiazine Defluorination Derivatives Domino reactions Fluorinated compounds Fluorination Fluorine Furanone synthesis Scaffolds Spiro annulation Transformations |
| title | Selectfluor‐Mediated Synthesis of Fluoro Spiro 3(2H)‐Furanone Derivatives via Domino Fluorination–Defluorination |
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