Synthesis of maleimide fused benzocarbazoles and imidazo[1,2- a ]pyridines via rhodium( iii )-catalyzed [4 + 2] oxidative cycloaddition
In this paper, an efficient and sustainable synthesis of the synthetically and pharmaceutically significant maleimide-fused benzocarbazoles/imidazo[1,2- a ]pyridines from the reaction of 2-arylindoles/2-arylimidazo[1,2- a ]pyridines with maleimides through rhodium-catalyzed oxidative [4 + 2] annulat...
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| Veröffentlicht in: | Organic Chemistry Frontiers 2020-11, Vol.7 (22), p.3698-3704 |
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| container_title | Organic Chemistry Frontiers |
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| creator | Li, Bin Guo, Chenhao Shen, Nana Zhang, Xinying Fan, Xuesen |
| description | In this paper, an efficient and sustainable synthesis of the synthetically and pharmaceutically significant maleimide-fused benzocarbazoles/imidazo[1,2-
a
]pyridines from the reaction of 2-arylindoles/2-arylimidazo[1,2-
a
]pyridines with maleimides through rhodium-catalyzed oxidative [4 + 2] annulation is presented. This method features easily obtainable substrates, high atom-efficiency and good functional group tolerance. Notably, by using this method a bioactive agent was smoothly synthesized in an excellent yield. |
| doi_str_mv | 10.1039/D0QO01109F |
| format | Article |
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a
]pyridines from the reaction of 2-arylindoles/2-arylimidazo[1,2-
a
]pyridines with maleimides through rhodium-catalyzed oxidative [4 + 2] annulation is presented. This method features easily obtainable substrates, high atom-efficiency and good functional group tolerance. Notably, by using this method a bioactive agent was smoothly synthesized in an excellent yield.</description><identifier>ISSN: 2052-4129</identifier><identifier>ISSN: 2052-4110</identifier><identifier>EISSN: 2052-4129</identifier><identifier>EISSN: 2052-4110</identifier><identifier>DOI: 10.1039/D0QO01109F</identifier><language>eng</language><publisher>London: Royal Society of Chemistry</publisher><subject>Atom economy ; Catalysis ; Chemical reactions ; Crystal structure ; Crystallography ; Cycloaddition ; Functional groups ; NMR ; Nuclear magnetic resonance ; Organic chemistry ; Pyridines ; Rhodium ; Substrates ; Synthesis</subject><ispartof>Organic Chemistry Frontiers, 2020-11, Vol.7 (22), p.3698-3704</ispartof><rights>Copyright Royal Society of Chemistry 2020</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c325t-d8111e05949dc297351e140313870e3eb33b3f2a85655ac5fe5b34e3012d06133</citedby><cites>FETCH-LOGICAL-c325t-d8111e05949dc297351e140313870e3eb33b3f2a85655ac5fe5b34e3012d06133</cites><orcidid>0000-0002-0145-5926 ; 0000-0002-3416-4623 ; 0000-0002-2040-6919</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27923,27924</link.rule.ids></links><search><creatorcontrib>Li, Bin</creatorcontrib><creatorcontrib>Guo, Chenhao</creatorcontrib><creatorcontrib>Shen, Nana</creatorcontrib><creatorcontrib>Zhang, Xinying</creatorcontrib><creatorcontrib>Fan, Xuesen</creatorcontrib><title>Synthesis of maleimide fused benzocarbazoles and imidazo[1,2- a ]pyridines via rhodium( iii )-catalyzed [4 + 2] oxidative cycloaddition</title><title>Organic Chemistry Frontiers</title><description>In this paper, an efficient and sustainable synthesis of the synthetically and pharmaceutically significant maleimide-fused benzocarbazoles/imidazo[1,2-
a
]pyridines from the reaction of 2-arylindoles/2-arylimidazo[1,2-
a
]pyridines with maleimides through rhodium-catalyzed oxidative [4 + 2] annulation is presented. This method features easily obtainable substrates, high atom-efficiency and good functional group tolerance. Notably, by using this method a bioactive agent was smoothly synthesized in an excellent yield.</description><subject>Atom economy</subject><subject>Catalysis</subject><subject>Chemical reactions</subject><subject>Crystal structure</subject><subject>Crystallography</subject><subject>Cycloaddition</subject><subject>Functional groups</subject><subject>NMR</subject><subject>Nuclear magnetic resonance</subject><subject>Organic chemistry</subject><subject>Pyridines</subject><subject>Rhodium</subject><subject>Substrates</subject><subject>Synthesis</subject><issn>2052-4129</issn><issn>2052-4110</issn><issn>2052-4129</issn><issn>2052-4110</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><recordid>eNpNUNtKw0AUXETBUvviFyz44i261yZ5lGpVEIqoT6WEze4J3ZJk625STH_A3zalgj6dc5g5M8wgdErJDSU8vb0nrzNCKUmnB2jAiGSRoCw9_Lcfo1EIK0IIZXJMZDxA329d3Swh2IBdgStVgq2sAVy0AQzOod46rXyutq6EgFVt8A7vzzm9ZhFWeLHuvDW27tGNVdgvnbFtdY6ttfgi0qpRZbftpeYCX2G2wO6rf2_sBrDudOmUMbaxrj5BR4UqA4x-5xB9TB_eJ0_Ry-zxeXL3EmnOZBOZhFIKRKYiNZqlMZcUqCCc8iQmwCHnPOcFU4kcS6m0LEDmXADvAxsyppwP0dled-3dZwuhyVau9XVvmTEhkzQWgiY963LP0t6F4KHI1t5WyncZJdmu6-yva_4DyDNv2g</recordid><startdate>20201121</startdate><enddate>20201121</enddate><creator>Li, Bin</creator><creator>Guo, Chenhao</creator><creator>Shen, Nana</creator><creator>Zhang, Xinying</creator><creator>Fan, Xuesen</creator><general>Royal Society of Chemistry</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7QO</scope><scope>7SR</scope><scope>8BQ</scope><scope>8FD</scope><scope>FR3</scope><scope>JG9</scope><scope>P64</scope><orcidid>https://orcid.org/0000-0002-0145-5926</orcidid><orcidid>https://orcid.org/0000-0002-3416-4623</orcidid><orcidid>https://orcid.org/0000-0002-2040-6919</orcidid></search><sort><creationdate>20201121</creationdate><title>Synthesis of maleimide fused benzocarbazoles and imidazo[1,2- a ]pyridines via rhodium( iii )-catalyzed [4 + 2] oxidative cycloaddition</title><author>Li, Bin ; Guo, Chenhao ; Shen, Nana ; Zhang, Xinying ; Fan, Xuesen</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c325t-d8111e05949dc297351e140313870e3eb33b3f2a85655ac5fe5b34e3012d06133</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><topic>Atom economy</topic><topic>Catalysis</topic><topic>Chemical reactions</topic><topic>Crystal structure</topic><topic>Crystallography</topic><topic>Cycloaddition</topic><topic>Functional groups</topic><topic>NMR</topic><topic>Nuclear magnetic resonance</topic><topic>Organic chemistry</topic><topic>Pyridines</topic><topic>Rhodium</topic><topic>Substrates</topic><topic>Synthesis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Li, Bin</creatorcontrib><creatorcontrib>Guo, Chenhao</creatorcontrib><creatorcontrib>Shen, Nana</creatorcontrib><creatorcontrib>Zhang, Xinying</creatorcontrib><creatorcontrib>Fan, Xuesen</creatorcontrib><collection>CrossRef</collection><collection>Biotechnology Research Abstracts</collection><collection>Engineered Materials Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>Materials Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><jtitle>Organic Chemistry Frontiers</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Li, Bin</au><au>Guo, Chenhao</au><au>Shen, Nana</au><au>Zhang, Xinying</au><au>Fan, Xuesen</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of maleimide fused benzocarbazoles and imidazo[1,2- a ]pyridines via rhodium( iii )-catalyzed [4 + 2] oxidative cycloaddition</atitle><jtitle>Organic Chemistry Frontiers</jtitle><date>2020-11-21</date><risdate>2020</risdate><volume>7</volume><issue>22</issue><spage>3698</spage><epage>3704</epage><pages>3698-3704</pages><issn>2052-4129</issn><issn>2052-4110</issn><eissn>2052-4129</eissn><eissn>2052-4110</eissn><abstract>In this paper, an efficient and sustainable synthesis of the synthetically and pharmaceutically significant maleimide-fused benzocarbazoles/imidazo[1,2-
a
]pyridines from the reaction of 2-arylindoles/2-arylimidazo[1,2-
a
]pyridines with maleimides through rhodium-catalyzed oxidative [4 + 2] annulation is presented. This method features easily obtainable substrates, high atom-efficiency and good functional group tolerance. Notably, by using this method a bioactive agent was smoothly synthesized in an excellent yield.</abstract><cop>London</cop><pub>Royal Society of Chemistry</pub><doi>10.1039/D0QO01109F</doi><tpages>7</tpages><orcidid>https://orcid.org/0000-0002-0145-5926</orcidid><orcidid>https://orcid.org/0000-0002-3416-4623</orcidid><orcidid>https://orcid.org/0000-0002-2040-6919</orcidid></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 2052-4129 |
| ispartof | Organic Chemistry Frontiers, 2020-11, Vol.7 (22), p.3698-3704 |
| issn | 2052-4129 2052-4110 2052-4129 2052-4110 |
| language | eng |
| recordid | cdi_proquest_journals_2458974418 |
| source | Royal Society Of Chemistry Journals 2008- |
| subjects | Atom economy Catalysis Chemical reactions Crystal structure Crystallography Cycloaddition Functional groups NMR Nuclear magnetic resonance Organic chemistry Pyridines Rhodium Substrates Synthesis |
| title | Synthesis of maleimide fused benzocarbazoles and imidazo[1,2- a ]pyridines via rhodium( iii )-catalyzed [4 + 2] oxidative cycloaddition |
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