Synthesis of profluorescent isoindoline nitroxides via palladium-catalysed Heck alkenylation
The synthesis of a new structural class of isoindoline nitroxides (aminoxyls), accessible via the palladium-catalysed Heck reaction, is presented. Reaction of the aryl bromoamine, 5-bromo-1,1,3,3-tetramethylisoindoline (4) or dibromoamine, 5,6-dibromo-1,1,3,3-tetramethylisoindoline (5) or the analog...
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| Veröffentlicht in: | Organic & biomolecular chemistry 2005-07, Vol.3 (14), p.2593-2598 |
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| container_issue | 14 |
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| container_title | Organic & biomolecular chemistry |
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| creator | Keddie, Daniel J Johnson, Therese E Arnold, Dennis P Bottle, Steven E |
| description | The synthesis of a new structural class of isoindoline nitroxides (aminoxyls), accessible via the palladium-catalysed Heck reaction, is presented. Reaction of the aryl bromoamine, 5-bromo-1,1,3,3-tetramethylisoindoline (4) or dibromoamine, 5,6-dibromo-1,1,3,3-tetramethylisoindoline (5) or the analogous bromonitroxides 6 and 7 with methyl acrylate gives the acrylate substituted tetramethylisoindoline amines 8 and 10 and nitroxides 12 and 14. Similarly, the reaction of the aryl bromides and dibromides 4-7 with methyl 4-vinylbenzoate gives the carboxystyryl substituted tetramethylisoindoline amines 9 and 11 and the analogous nitroxides 13 and 15. The carboxystyryl tetramethylisoindoline nitroxides demonstrate strongly suppressed fluorescence, which is revealed upon removal of the free radical by reduction or radical coupling. |
| doi_str_mv | 10.1039/b504354a |
| format | Article |
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Reaction of the aryl bromoamine, 5-bromo-1,1,3,3-tetramethylisoindoline (4) or dibromoamine, 5,6-dibromo-1,1,3,3-tetramethylisoindoline (5) or the analogous bromonitroxides 6 and 7 with methyl acrylate gives the acrylate substituted tetramethylisoindoline amines 8 and 10 and nitroxides 12 and 14. Similarly, the reaction of the aryl bromides and dibromides 4-7 with methyl 4-vinylbenzoate gives the carboxystyryl substituted tetramethylisoindoline amines 9 and 11 and the analogous nitroxides 13 and 15. The carboxystyryl tetramethylisoindoline nitroxides demonstrate strongly suppressed fluorescence, which is revealed upon removal of the free radical by reduction or radical coupling.</description><identifier>ISSN: 1477-0520</identifier><identifier>EISSN: 1477-0539</identifier><identifier>DOI: 10.1039/b504354a</identifier><identifier>PMID: 15999192</identifier><language>eng</language><publisher>England</publisher><subject>Alkenes - chemistry ; Antioxidants - chemical synthesis ; Antioxidants - chemistry ; Catalysis ; Fluorescence ; Indoles - chemical synthesis ; Indoles - chemistry ; Molecular Structure ; Nitrogen Oxides - chemical synthesis ; Nitrogen Oxides - chemistry ; Palladium - chemistry ; Stilbenes - chemistry</subject><ispartof>Organic & biomolecular chemistry, 2005-07, Vol.3 (14), p.2593-2598</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c301t-d9300df9e93697a377c67dd4e874d8fb01a6a2eb638af6ff790bbe5f1fb639b73</citedby><cites>FETCH-LOGICAL-c301t-d9300df9e93697a377c67dd4e874d8fb01a6a2eb638af6ff790bbe5f1fb639b73</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,2818,27901,27902</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/15999192$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Keddie, Daniel J</creatorcontrib><creatorcontrib>Johnson, Therese E</creatorcontrib><creatorcontrib>Arnold, Dennis P</creatorcontrib><creatorcontrib>Bottle, Steven E</creatorcontrib><title>Synthesis of profluorescent isoindoline nitroxides via palladium-catalysed Heck alkenylation</title><title>Organic & biomolecular chemistry</title><addtitle>Org Biomol Chem</addtitle><description>The synthesis of a new structural class of isoindoline nitroxides (aminoxyls), accessible via the palladium-catalysed Heck reaction, is presented. Reaction of the aryl bromoamine, 5-bromo-1,1,3,3-tetramethylisoindoline (4) or dibromoamine, 5,6-dibromo-1,1,3,3-tetramethylisoindoline (5) or the analogous bromonitroxides 6 and 7 with methyl acrylate gives the acrylate substituted tetramethylisoindoline amines 8 and 10 and nitroxides 12 and 14. Similarly, the reaction of the aryl bromides and dibromides 4-7 with methyl 4-vinylbenzoate gives the carboxystyryl substituted tetramethylisoindoline amines 9 and 11 and the analogous nitroxides 13 and 15. The carboxystyryl tetramethylisoindoline nitroxides demonstrate strongly suppressed fluorescence, which is revealed upon removal of the free radical by reduction or radical coupling.</description><subject>Alkenes - chemistry</subject><subject>Antioxidants - chemical synthesis</subject><subject>Antioxidants - chemistry</subject><subject>Catalysis</subject><subject>Fluorescence</subject><subject>Indoles - chemical synthesis</subject><subject>Indoles - chemistry</subject><subject>Molecular Structure</subject><subject>Nitrogen Oxides - chemical synthesis</subject><subject>Nitrogen Oxides - chemistry</subject><subject>Palladium - chemistry</subject><subject>Stilbenes - chemistry</subject><issn>1477-0520</issn><issn>1477-0539</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2005</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpFkMFKxDAQhoMo7roKPoHkJF6qk03bNEdZVldY8KDehJI2E4ybJmvTin17K7vqaYbh4-efj5BzBtcMuLypMkh5lqoDMmWpEAlkXB7-7XOYkJMY3wGYFHl6TCYsk1IyOZ-S16fBd28YbaTB0G0bjOtDi7FG31Ebg_U6OOuRetu14ctqjPTTKrpVzilt-yapVafcEFHTFdYbqtwG_eBUZ4M_JUdGuYhn-zkjL3fL58UqWT_ePyxu10nNgXWJlhxAG4mS51IoLkSdC61TLESqC1MBU7maY5XzQpncGCGhqjAzzIwnWQk-I5e73LH_R4-xKxs7fjA29Bj6WOYFgGQCRvBqB9ZtiLFFU25b26h2KBmUPybLX5MjerHP7KsG9T-4V8e_ATMAcKs</recordid><startdate>20050721</startdate><enddate>20050721</enddate><creator>Keddie, Daniel J</creator><creator>Johnson, Therese E</creator><creator>Arnold, Dennis P</creator><creator>Bottle, Steven E</creator><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20050721</creationdate><title>Synthesis of profluorescent isoindoline nitroxides via palladium-catalysed Heck alkenylation</title><author>Keddie, Daniel J ; Johnson, Therese E ; Arnold, Dennis P ; Bottle, Steven E</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c301t-d9300df9e93697a377c67dd4e874d8fb01a6a2eb638af6ff790bbe5f1fb639b73</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2005</creationdate><topic>Alkenes - chemistry</topic><topic>Antioxidants - chemical synthesis</topic><topic>Antioxidants - chemistry</topic><topic>Catalysis</topic><topic>Fluorescence</topic><topic>Indoles - chemical synthesis</topic><topic>Indoles - chemistry</topic><topic>Molecular Structure</topic><topic>Nitrogen Oxides - chemical synthesis</topic><topic>Nitrogen Oxides - chemistry</topic><topic>Palladium - chemistry</topic><topic>Stilbenes - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Keddie, Daniel J</creatorcontrib><creatorcontrib>Johnson, Therese E</creatorcontrib><creatorcontrib>Arnold, Dennis P</creatorcontrib><creatorcontrib>Bottle, Steven E</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Organic & biomolecular chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Keddie, Daniel J</au><au>Johnson, Therese E</au><au>Arnold, Dennis P</au><au>Bottle, Steven E</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of profluorescent isoindoline nitroxides via palladium-catalysed Heck alkenylation</atitle><jtitle>Organic & biomolecular chemistry</jtitle><addtitle>Org Biomol Chem</addtitle><date>2005-07-21</date><risdate>2005</risdate><volume>3</volume><issue>14</issue><spage>2593</spage><epage>2598</epage><pages>2593-2598</pages><issn>1477-0520</issn><eissn>1477-0539</eissn><abstract>The synthesis of a new structural class of isoindoline nitroxides (aminoxyls), accessible via the palladium-catalysed Heck reaction, is presented. Reaction of the aryl bromoamine, 5-bromo-1,1,3,3-tetramethylisoindoline (4) or dibromoamine, 5,6-dibromo-1,1,3,3-tetramethylisoindoline (5) or the analogous bromonitroxides 6 and 7 with methyl acrylate gives the acrylate substituted tetramethylisoindoline amines 8 and 10 and nitroxides 12 and 14. Similarly, the reaction of the aryl bromides and dibromides 4-7 with methyl 4-vinylbenzoate gives the carboxystyryl substituted tetramethylisoindoline amines 9 and 11 and the analogous nitroxides 13 and 15. The carboxystyryl tetramethylisoindoline nitroxides demonstrate strongly suppressed fluorescence, which is revealed upon removal of the free radical by reduction or radical coupling.</abstract><cop>England</cop><pmid>15999192</pmid><doi>10.1039/b504354a</doi><tpages>6</tpages></addata></record> |
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| ispartof | Organic & biomolecular chemistry, 2005-07, Vol.3 (14), p.2593-2598 |
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| source | Royal Society of Chemistry Journals Archive (1841-2007); MEDLINE; Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Alkenes - chemistry Antioxidants - chemical synthesis Antioxidants - chemistry Catalysis Fluorescence Indoles - chemical synthesis Indoles - chemistry Molecular Structure Nitrogen Oxides - chemical synthesis Nitrogen Oxides - chemistry Palladium - chemistry Stilbenes - chemistry |
| title | Synthesis of profluorescent isoindoline nitroxides via palladium-catalysed Heck alkenylation |
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