Syntheses of three naturally occurring polybrominated 3,3′-bi-1H-indoles
[Display omitted] •Syntheses of three polybrominated biindole alkaloids have been completed.•A palladium catalyzed reductive cyclization was used as key ring-closing step.•N-bromosuccinimide was used brominate the biindoles. The naturally occurring polybrominated indoles 2,2′,5,5′-tetrabromo-3,3′-bi...
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| Veröffentlicht in: | Tetrahedron letters 2017-03, Vol.58 (11), p.1053-1056 |
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| creator | Ansari, Nurul H. Taylor, Matthew C. Söderberg, Björn C.G. |
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•Syntheses of three polybrominated biindole alkaloids have been completed.•A palladium catalyzed reductive cyclization was used as key ring-closing step.•N-bromosuccinimide was used brominate the biindoles.
The naturally occurring polybrominated indoles 2,2′,5,5′-tetrabromo-3,3′-bi-1H-indole, 2,2′,6,6′-tetrabromo-3,3′-bi-1H-indole, and 2,2′,5,5′,6,6′-hexabromo-3,3′-bi-1H-indole were synthesized using a palladium catalyzed, carbon monoxide mediated, double reductive N-heterocyclization of 2,3-bis(2-nitro-4(or 5)-bromophenyl)-1,4-butadienes as the key step. |
| doi_str_mv | 10.1016/j.tetlet.2017.01.103 |
| format | Article |
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•Syntheses of three polybrominated biindole alkaloids have been completed.•A palladium catalyzed reductive cyclization was used as key ring-closing step.•N-bromosuccinimide was used brominate the biindoles.
The naturally occurring polybrominated indoles 2,2′,5,5′-tetrabromo-3,3′-bi-1H-indole, 2,2′,6,6′-tetrabromo-3,3′-bi-1H-indole, and 2,2′,5,5′,6,6′-hexabromo-3,3′-bi-1H-indole were synthesized using a palladium catalyzed, carbon monoxide mediated, double reductive N-heterocyclization of 2,3-bis(2-nitro-4(or 5)-bromophenyl)-1,4-butadienes as the key step.</description><identifier>ISSN: 0040-4039</identifier><identifier>EISSN: 1873-3581</identifier><identifier>DOI: 10.1016/j.tetlet.2017.01.103</identifier><identifier>PMID: 28966402</identifier><language>eng</language><publisher>Elsevier Ltd</publisher><subject>carbon monoxide ; Catalysis ; catalysts ; chemical reactions ; chemical structure ; Cyclization ; indoles ; organobromine compounds ; Palladium ; Polybrominated biindoles</subject><ispartof>Tetrahedron letters, 2017-03, Vol.58 (11), p.1053-1056</ispartof><rights>2017 Elsevier Ltd</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c473t-3ef7cf02bfd0278d3975b9c616bcdff01593f2ad34d8bc5ddf15d5c73cc20baa3</citedby><cites>FETCH-LOGICAL-c473t-3ef7cf02bfd0278d3975b9c616bcdff01593f2ad34d8bc5ddf15d5c73cc20baa3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.tetlet.2017.01.103$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>230,314,777,781,882,3537,27905,27906,45976</link.rule.ids></links><search><creatorcontrib>Ansari, Nurul H.</creatorcontrib><creatorcontrib>Taylor, Matthew C.</creatorcontrib><creatorcontrib>Söderberg, Björn C.G.</creatorcontrib><title>Syntheses of three naturally occurring polybrominated 3,3′-bi-1H-indoles</title><title>Tetrahedron letters</title><description>[Display omitted]
•Syntheses of three polybrominated biindole alkaloids have been completed.•A palladium catalyzed reductive cyclization was used as key ring-closing step.•N-bromosuccinimide was used brominate the biindoles.
The naturally occurring polybrominated indoles 2,2′,5,5′-tetrabromo-3,3′-bi-1H-indole, 2,2′,6,6′-tetrabromo-3,3′-bi-1H-indole, and 2,2′,5,5′,6,6′-hexabromo-3,3′-bi-1H-indole were synthesized using a palladium catalyzed, carbon monoxide mediated, double reductive N-heterocyclization of 2,3-bis(2-nitro-4(or 5)-bromophenyl)-1,4-butadienes as the key step.</description><subject>carbon monoxide</subject><subject>Catalysis</subject><subject>catalysts</subject><subject>chemical reactions</subject><subject>chemical structure</subject><subject>Cyclization</subject><subject>indoles</subject><subject>organobromine compounds</subject><subject>Palladium</subject><subject>Polybrominated biindoles</subject><issn>0040-4039</issn><issn>1873-3581</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2017</creationdate><recordtype>article</recordtype><recordid>eNqFUUFuFDEQtBCIbAI_4DBHDsxiu8f2zAUJRZCAInEgOVseu531ana82J5Ie-NNPCkvwdFGIC6hLy11lUrVVYS8YXTNKJPvt-uCZcKy5pSpNWX1Cs_IivUKWhA9e05WlHa07SgMJ-Q05y2tI3v6kpzwfpCyo3xFvn4_zGWDGXMTfVM2CbGZTVmSmaZDE61dUgrzbbOP02FMcRcqiK6Bd3D_81c7hpZdtmF2ccL8irzwZsr4-nGfkZvPn67PL9urbxdfzj9etbZTUFpAr6ynfPSOctU7GJQYByuZHK3znjIxgOfGQef60QrnPBNOWAXWcjoaA2fkw1F3v4w7dBbnUt3qfQo7kw46mqD_Reaw0bfxTgvJlIShCrx9FEjxx4K56F3IFqfJzBiXrHnNCYQEYP-lsqETivUDV5XaHak2xZwT-j-OGNUPjemtPjamHxrTlNUr_P0Ga2R3AZPONuBs0YWEtmgXw9MCvwGEsqI2</recordid><startdate>20170315</startdate><enddate>20170315</enddate><creator>Ansari, Nurul H.</creator><creator>Taylor, Matthew C.</creator><creator>Söderberg, Björn C.G.</creator><general>Elsevier Ltd</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope><scope>7S9</scope><scope>L.6</scope><scope>5PM</scope></search><sort><creationdate>20170315</creationdate><title>Syntheses of three naturally occurring polybrominated 3,3′-bi-1H-indoles</title><author>Ansari, Nurul H. ; Taylor, Matthew C. ; Söderberg, Björn C.G.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c473t-3ef7cf02bfd0278d3975b9c616bcdff01593f2ad34d8bc5ddf15d5c73cc20baa3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2017</creationdate><topic>carbon monoxide</topic><topic>Catalysis</topic><topic>catalysts</topic><topic>chemical reactions</topic><topic>chemical structure</topic><topic>Cyclization</topic><topic>indoles</topic><topic>organobromine compounds</topic><topic>Palladium</topic><topic>Polybrominated biindoles</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ansari, Nurul H.</creatorcontrib><creatorcontrib>Taylor, Matthew C.</creatorcontrib><creatorcontrib>Söderberg, Björn C.G.</creatorcontrib><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><collection>AGRICOLA</collection><collection>AGRICOLA - Academic</collection><collection>PubMed Central (Full Participant titles)</collection><jtitle>Tetrahedron letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Ansari, Nurul H.</au><au>Taylor, Matthew C.</au><au>Söderberg, Björn C.G.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Syntheses of three naturally occurring polybrominated 3,3′-bi-1H-indoles</atitle><jtitle>Tetrahedron letters</jtitle><date>2017-03-15</date><risdate>2017</risdate><volume>58</volume><issue>11</issue><spage>1053</spage><epage>1056</epage><pages>1053-1056</pages><issn>0040-4039</issn><eissn>1873-3581</eissn><abstract>[Display omitted]
•Syntheses of three polybrominated biindole alkaloids have been completed.•A palladium catalyzed reductive cyclization was used as key ring-closing step.•N-bromosuccinimide was used brominate the biindoles.
The naturally occurring polybrominated indoles 2,2′,5,5′-tetrabromo-3,3′-bi-1H-indole, 2,2′,6,6′-tetrabromo-3,3′-bi-1H-indole, and 2,2′,5,5′,6,6′-hexabromo-3,3′-bi-1H-indole were synthesized using a palladium catalyzed, carbon monoxide mediated, double reductive N-heterocyclization of 2,3-bis(2-nitro-4(or 5)-bromophenyl)-1,4-butadienes as the key step.</abstract><pub>Elsevier Ltd</pub><pmid>28966402</pmid><doi>10.1016/j.tetlet.2017.01.103</doi><tpages>4</tpages><oa>free_for_read</oa></addata></record> |
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| source | Elsevier ScienceDirect Journals |
| subjects | carbon monoxide Catalysis catalysts chemical reactions chemical structure Cyclization indoles organobromine compounds Palladium Polybrominated biindoles |
| title | Syntheses of three naturally occurring polybrominated 3,3′-bi-1H-indoles |
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