Regioselective, Solvent- and Metal-Free Chalcogenation of Imidazo[1,2-a]pyridines by Employing I2/DMSO as the Catalytic Oxidation System
Highly efficient molecular‐iodine‐catalyzed chalcogenations (S and Se) of imidazo[1,2‐a]pyridines were achieved by using diorganoyl dichalcogenides under solvent‐free conditions. This approach afforded the desired products that had been chalcogenated regioselectively at the C3 position in up to 96 %...
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| Veröffentlicht in: | Chemistry : a European journal 2016-08, Vol.22 (33), p.11854-11862 |
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| container_issue | 33 |
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| container_title | Chemistry : a European journal |
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| creator | Rafique, Jamal Saba, Sumbal Rosário, Alisson R. Braga, Antonio L. |
| description | Highly efficient molecular‐iodine‐catalyzed chalcogenations (S and Se) of imidazo[1,2‐a]pyridines were achieved by using diorganoyl dichalcogenides under solvent‐free conditions. This approach afforded the desired products that had been chalcogenated regioselectively at the C3 position in up to 96 % yield by using DMSO as an oxidant, in the absence of a metal catalyst, and under an inert atmosphere. This mild, green approach allowed the preparation of different types of chalcogenated imidazo[1,2‐a]pyridines with structural diversity. Furthermore, the current protocol was also extended to other N‐heterocyclic cores.
Chalcogenation of N‐heterocycles: Highly efficient molecular‐iodine‐catalyzed chalcogenations (S and Se) of imidazo[1,2‐a]pyridines are achieved by using diorganoyl dichalcogenides under solvent‐free conditions. |
| doi_str_mv | 10.1002/chem.201600800 |
| format | Article |
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Chalcogenation of N‐heterocycles: Highly efficient molecular‐iodine‐catalyzed chalcogenations (S and Se) of imidazo[1,2‐a]pyridines are achieved by using diorganoyl dichalcogenides under solvent‐free conditions.</description><identifier>ISSN: 0947-6539</identifier><identifier>EISSN: 1521-3765</identifier><identifier>DOI: 10.1002/chem.201600800</identifier><identifier>PMID: 27388454</identifier><identifier>CODEN: CEUJED</identifier><language>eng</language><publisher>Germany: Blackwell Publishing Ltd</publisher><subject>Atmosphere ; Catalysts ; Catalytic oxidation ; Chemistry ; Cores ; green chemistry ; Iodine ; Metals ; nitrogen heterocycles ; Oxidation ; Pyridines ; Regioselectivity ; selenium ; Solvents ; sulfur ; Yield</subject><ispartof>Chemistry : a European journal, 2016-08, Vol.22 (33), p.11854-11862</ispartof><rights>2016 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><rights>2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.</rights><rights>2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><orcidid>0000-0001-9713-2189 ; 0000-0002-2336-040X ; 0000-0002-6134-7249 ; 0000-0001-9903-6764</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%2Fchem.201600800$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fchem.201600800$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>315,781,785,1418,27929,27930,45579,45580</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/27388454$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Rafique, Jamal</creatorcontrib><creatorcontrib>Saba, Sumbal</creatorcontrib><creatorcontrib>Rosário, Alisson R.</creatorcontrib><creatorcontrib>Braga, Antonio L.</creatorcontrib><title>Regioselective, Solvent- and Metal-Free Chalcogenation of Imidazo[1,2-a]pyridines by Employing I2/DMSO as the Catalytic Oxidation System</title><title>Chemistry : a European journal</title><addtitle>Chem. Eur. J</addtitle><description>Highly efficient molecular‐iodine‐catalyzed chalcogenations (S and Se) of imidazo[1,2‐a]pyridines were achieved by using diorganoyl dichalcogenides under solvent‐free conditions. This approach afforded the desired products that had been chalcogenated regioselectively at the C3 position in up to 96 % yield by using DMSO as an oxidant, in the absence of a metal catalyst, and under an inert atmosphere. This mild, green approach allowed the preparation of different types of chalcogenated imidazo[1,2‐a]pyridines with structural diversity. Furthermore, the current protocol was also extended to other N‐heterocyclic cores.
Chalcogenation of N‐heterocycles: Highly efficient molecular‐iodine‐catalyzed chalcogenations (S and Se) of imidazo[1,2‐a]pyridines are achieved by using diorganoyl dichalcogenides under solvent‐free conditions.</description><subject>Atmosphere</subject><subject>Catalysts</subject><subject>Catalytic oxidation</subject><subject>Chemistry</subject><subject>Cores</subject><subject>green chemistry</subject><subject>Iodine</subject><subject>Metals</subject><subject>nitrogen heterocycles</subject><subject>Oxidation</subject><subject>Pyridines</subject><subject>Regioselectivity</subject><subject>selenium</subject><subject>Solvents</subject><subject>sulfur</subject><subject>Yield</subject><issn>0947-6539</issn><issn>1521-3765</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><recordid>eNp9kU1vEzEQhlcIREPhyhFZ4sKh244_dm0f0ZK2kRoikUAlELIc7yRx2Y-w3pQuv4CfjUtKDhw4jUbzvK9m5k2SlxROKQA7cxusTxnQHEABPEpGNGM05TLPHicj0EKmecb1UfIshBsA0DnnT5MjJrlSIhOj5NcHXPs2YIWu97d4QuZtdYtNnxLblGSKva3S8w6RFBtbuXaNje1925B2RSa1L-3P9gs9Yan9uh06X_oGA1kOZFxvq3bwzZpM2Nm76XxGbCD9JrrYaDj03pHZXVT_sZoPocf6efJkZauALx7qcfLxfLwoLtOr2cWkeHuVrkWmIC2XKKTmOVNOca0kKhBaiRWTIIRmTivEFWc0Z9I51Nwtde5UqRSNc7fk_Dh5s_fddu33HYbe1D44rCrbYLsLhipQXEkuRURf_4PetLuuidsZqkFywXLQ_6UUSJXrDLJIvXqgdssaS7PtfG27wfxNIgJ6D_zwFQ6HOQVzn7O5z9kccjbF5Xh66KI23Wt9_OTdQWu7byaPl2Tm-v2FWWTF4nr6mZlP_Dc1pKib</recordid><startdate>20160808</startdate><enddate>20160808</enddate><creator>Rafique, Jamal</creator><creator>Saba, Sumbal</creator><creator>Rosário, Alisson R.</creator><creator>Braga, Antonio L.</creator><general>Blackwell Publishing Ltd</general><general>Wiley Subscription Services, Inc</general><scope>BSCLL</scope><scope>NPM</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>K9.</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0001-9713-2189</orcidid><orcidid>https://orcid.org/0000-0002-2336-040X</orcidid><orcidid>https://orcid.org/0000-0002-6134-7249</orcidid><orcidid>https://orcid.org/0000-0001-9903-6764</orcidid></search><sort><creationdate>20160808</creationdate><title>Regioselective, Solvent- and Metal-Free Chalcogenation of Imidazo[1,2-a]pyridines by Employing I2/DMSO as the Catalytic Oxidation System</title><author>Rafique, Jamal ; Saba, Sumbal ; Rosário, Alisson R. ; Braga, Antonio L.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-g4580-dbe4793628c83987e804984f2704492c98eef321627cce93cb96c8d881044cb33</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2016</creationdate><topic>Atmosphere</topic><topic>Catalysts</topic><topic>Catalytic oxidation</topic><topic>Chemistry</topic><topic>Cores</topic><topic>green chemistry</topic><topic>Iodine</topic><topic>Metals</topic><topic>nitrogen heterocycles</topic><topic>Oxidation</topic><topic>Pyridines</topic><topic>Regioselectivity</topic><topic>selenium</topic><topic>Solvents</topic><topic>sulfur</topic><topic>Yield</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Rafique, Jamal</creatorcontrib><creatorcontrib>Saba, Sumbal</creatorcontrib><creatorcontrib>Rosário, Alisson R.</creatorcontrib><creatorcontrib>Braga, Antonio L.</creatorcontrib><collection>Istex</collection><collection>PubMed</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>ProQuest Health & Medical Complete (Alumni)</collection><collection>MEDLINE - Academic</collection><jtitle>Chemistry : a European journal</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Rafique, Jamal</au><au>Saba, Sumbal</au><au>Rosário, Alisson R.</au><au>Braga, Antonio L.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Regioselective, Solvent- and Metal-Free Chalcogenation of Imidazo[1,2-a]pyridines by Employing I2/DMSO as the Catalytic Oxidation System</atitle><jtitle>Chemistry : a European journal</jtitle><addtitle>Chem. Eur. J</addtitle><date>2016-08-08</date><risdate>2016</risdate><volume>22</volume><issue>33</issue><spage>11854</spage><epage>11862</epage><pages>11854-11862</pages><issn>0947-6539</issn><eissn>1521-3765</eissn><coden>CEUJED</coden><abstract>Highly efficient molecular‐iodine‐catalyzed chalcogenations (S and Se) of imidazo[1,2‐a]pyridines were achieved by using diorganoyl dichalcogenides under solvent‐free conditions. This approach afforded the desired products that had been chalcogenated regioselectively at the C3 position in up to 96 % yield by using DMSO as an oxidant, in the absence of a metal catalyst, and under an inert atmosphere. This mild, green approach allowed the preparation of different types of chalcogenated imidazo[1,2‐a]pyridines with structural diversity. Furthermore, the current protocol was also extended to other N‐heterocyclic cores.
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| subjects | Atmosphere Catalysts Catalytic oxidation Chemistry Cores green chemistry Iodine Metals nitrogen heterocycles Oxidation Pyridines Regioselectivity selenium Solvents sulfur Yield |
| title | Regioselective, Solvent- and Metal-Free Chalcogenation of Imidazo[1,2-a]pyridines by Employing I2/DMSO as the Catalytic Oxidation System |
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