Orthogonal Synthesis of Fluorinated Acridones and Acridines from Perfluorobenzophenone
The reaction between perfluorobenzophenone and aromatic amines proceeds with the substitution of one or more fluorine atoms. The regiochemistry of this substitution is controlled by solvent polarity, temperature, and nucleophilic character of the amine. o‐Anilinononafluorobenzophenone can be selecti...
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| Veröffentlicht in: | European Journal of Organic Chemistry 2011-04, Vol.2011 (12), p.2265-2271 |
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| container_issue | 12 |
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| container_title | European Journal of Organic Chemistry |
| container_volume | 2011 |
| creator | Del Buttero, Paola Gironda, Ramona Moret, Massimo Papagni, Antonio Parravicini, Matteo Rizzato, Silvia Miozzo, Luciano |
| description | The reaction between perfluorobenzophenone and aromatic amines proceeds with the substitution of one or more fluorine atoms. The regiochemistry of this substitution is controlled by solvent polarity, temperature, and nucleophilic character of the amine. o‐Anilinononafluorobenzophenone can be selectively transformed into acridines or acridones by using acid or base catalysis through electrocyclization or aromatic nucleophilic substitution.
The reaction of decafluorobenzophenone with anilines produces the corresponding para‐anilino‐substituted derivatives, and the ortho/para ratio is strongly influenced by the donor number. The ortho isomers can be, in turn, selectively transformed into acridines and acridones under strongly acidic or basic conditions. |
| doi_str_mv | 10.1002/ejoc.201001647 |
| format | Article |
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The reaction of decafluorobenzophenone with anilines produces the corresponding para‐anilino‐substituted derivatives, and the ortho/para ratio is strongly influenced by the donor number. The ortho isomers can be, in turn, selectively transformed into acridines and acridones under strongly acidic or basic conditions.</description><identifier>ISSN: 1434-193X</identifier><identifier>EISSN: 1099-0690</identifier><identifier>DOI: 10.1002/ejoc.201001647</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>Chemistry ; Exact sciences and technology ; Fluorine ; Heterocyclic compounds ; Heterocyclic compounds with only one n hetero atom and condensed derivatives ; Nitrogen heterocycles ; Noncondensed benzenic compounds ; Nucleophilic substitution ; Organic chemistry ; Pericyclic reactions ; Preparations and properties ; Solvent effects</subject><ispartof>European Journal of Organic Chemistry, 2011-04, Vol.2011 (12), p.2265-2271</ispartof><rights>Copyright © 2011 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2015 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3577-328fd5532a88d5f70949f3e23b853019c95b212b23d960834d64e6ccf5c172933</citedby><cites>FETCH-LOGICAL-c3577-328fd5532a88d5f70949f3e23b853019c95b212b23d960834d64e6ccf5c172933</cites></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.201001647$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fejoc.201001647$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>313,314,778,782,790,1414,27905,27907,27908,45557,45558</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=24090994$$DView record in Pascal Francis$$Hfree_for_read</backlink></links><search><creatorcontrib>Del Buttero, Paola</creatorcontrib><creatorcontrib>Gironda, Ramona</creatorcontrib><creatorcontrib>Moret, Massimo</creatorcontrib><creatorcontrib>Papagni, Antonio</creatorcontrib><creatorcontrib>Parravicini, Matteo</creatorcontrib><creatorcontrib>Rizzato, Silvia</creatorcontrib><creatorcontrib>Miozzo, Luciano</creatorcontrib><title>Orthogonal Synthesis of Fluorinated Acridones and Acridines from Perfluorobenzophenone</title><title>European Journal of Organic Chemistry</title><addtitle>Eur. J. Org. Chem</addtitle><description>The reaction between perfluorobenzophenone and aromatic amines proceeds with the substitution of one or more fluorine atoms. The regiochemistry of this substitution is controlled by solvent polarity, temperature, and nucleophilic character of the amine. o‐Anilinononafluorobenzophenone can be selectively transformed into acridines or acridones by using acid or base catalysis through electrocyclization or aromatic nucleophilic substitution.
The reaction of decafluorobenzophenone with anilines produces the corresponding para‐anilino‐substituted derivatives, and the ortho/para ratio is strongly influenced by the donor number. The ortho isomers can be, in turn, selectively transformed into acridines and acridones under strongly acidic or basic conditions.</description><subject>Chemistry</subject><subject>Exact sciences and technology</subject><subject>Fluorine</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with only one n hetero atom and condensed derivatives</subject><subject>Nitrogen heterocycles</subject><subject>Noncondensed benzenic compounds</subject><subject>Nucleophilic substitution</subject><subject>Organic chemistry</subject><subject>Pericyclic reactions</subject><subject>Preparations and properties</subject><subject>Solvent effects</subject><issn>1434-193X</issn><issn>1099-0690</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2011</creationdate><recordtype>article</recordtype><recordid>eNqFkLtPwzAYxCMEEqWwMmdhTPE78ViVtjwqWony2CzHsalLGld2EJS_nkSpKjam7066333SRdElBAMIALrWa6cGCDQaMpIeRT0IOE8A4-C40QSTBHL8dhqdhbAGAHDGYC96mft65d5dJcv4aVfVKx1siJ2JJ-Wn87aStS7iofK2cJUOsaz2zrbOeLeJF9qbNutyXf247UpXTfI8OjGyDPpif_vR82S8HN0ms_n0bjScJQrTNE0wykxBKUYyywpqUsAJN1gjnGcUA8gVpzmCKEe44AxkmBSMaKaUoQqmiGPcjwZdr_IuBK-N2Hq7kX4nIBDtKqJdRRxWaYCrDtjKoGRpvKyUDQcKEcCb1UiT413uy5Z690-rGN_PR39_JB1rQ62_D6z0H4KlOKXi9XEq-Gz5AKc3UCzwL0kAgxo</recordid><startdate>201104</startdate><enddate>201104</enddate><creator>Del Buttero, Paola</creator><creator>Gironda, Ramona</creator><creator>Moret, Massimo</creator><creator>Papagni, Antonio</creator><creator>Parravicini, Matteo</creator><creator>Rizzato, Silvia</creator><creator>Miozzo, Luciano</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><general>Wiley-VCH</general><scope>BSCLL</scope><scope>IQODW</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>201104</creationdate><title>Orthogonal Synthesis of Fluorinated Acridones and Acridines from Perfluorobenzophenone</title><author>Del Buttero, Paola ; Gironda, Ramona ; Moret, Massimo ; Papagni, Antonio ; Parravicini, Matteo ; Rizzato, Silvia ; Miozzo, Luciano</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3577-328fd5532a88d5f70949f3e23b853019c95b212b23d960834d64e6ccf5c172933</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2011</creationdate><topic>Chemistry</topic><topic>Exact sciences and technology</topic><topic>Fluorine</topic><topic>Heterocyclic compounds</topic><topic>Heterocyclic compounds with only one n hetero atom and condensed derivatives</topic><topic>Nitrogen heterocycles</topic><topic>Noncondensed benzenic compounds</topic><topic>Nucleophilic substitution</topic><topic>Organic chemistry</topic><topic>Pericyclic reactions</topic><topic>Preparations and properties</topic><topic>Solvent effects</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Del Buttero, Paola</creatorcontrib><creatorcontrib>Gironda, Ramona</creatorcontrib><creatorcontrib>Moret, Massimo</creatorcontrib><creatorcontrib>Papagni, Antonio</creatorcontrib><creatorcontrib>Parravicini, Matteo</creatorcontrib><creatorcontrib>Rizzato, Silvia</creatorcontrib><creatorcontrib>Miozzo, Luciano</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><collection>CrossRef</collection><jtitle>European Journal of Organic Chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Del Buttero, Paola</au><au>Gironda, Ramona</au><au>Moret, Massimo</au><au>Papagni, Antonio</au><au>Parravicini, Matteo</au><au>Rizzato, Silvia</au><au>Miozzo, Luciano</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Orthogonal Synthesis of Fluorinated Acridones and Acridines from Perfluorobenzophenone</atitle><jtitle>European Journal of Organic Chemistry</jtitle><addtitle>Eur. J. Org. Chem</addtitle><date>2011-04</date><risdate>2011</risdate><volume>2011</volume><issue>12</issue><spage>2265</spage><epage>2271</epage><pages>2265-2271</pages><issn>1434-193X</issn><eissn>1099-0690</eissn><abstract>The reaction between perfluorobenzophenone and aromatic amines proceeds with the substitution of one or more fluorine atoms. The regiochemistry of this substitution is controlled by solvent polarity, temperature, and nucleophilic character of the amine. o‐Anilinononafluorobenzophenone can be selectively transformed into acridines or acridones by using acid or base catalysis through electrocyclization or aromatic nucleophilic substitution.
The reaction of decafluorobenzophenone with anilines produces the corresponding para‐anilino‐substituted derivatives, and the ortho/para ratio is strongly influenced by the donor number. The ortho isomers can be, in turn, selectively transformed into acridines and acridones under strongly acidic or basic conditions.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><doi>10.1002/ejoc.201001647</doi><tpages>7</tpages></addata></record> |
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| source | Wiley Online Library Journals Frontfile Complete |
| subjects | Chemistry Exact sciences and technology Fluorine Heterocyclic compounds Heterocyclic compounds with only one n hetero atom and condensed derivatives Nitrogen heterocycles Noncondensed benzenic compounds Nucleophilic substitution Organic chemistry Pericyclic reactions Preparations and properties Solvent effects |
| title | Orthogonal Synthesis of Fluorinated Acridones and Acridines from Perfluorobenzophenone |
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