Synthesis of benzo[b][1,5]diazocin-6(5H)-one derivatives via the Cu-catalysed oxidative cyclization of 2-aryl-1H-indoles with 1,1-enediamines
A novel protocol for the synthesis of highly functionalized benzo[b][1,5]diazocin-6(5H)-one derivatives (BDCOs, 4 and 5) from 2-aryl-1H-indoles and 1,1-enediamines was developed via a complex cascade of reactions including regioselective free radical oxidation, the 1,2-addition of imine, imine–enami...
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| Veröffentlicht in: | Chemical communications (Cambridge, England) England), 2023-01, Vol.59 (9), p.1217-1220 |
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| container_title | Chemical communications (Cambridge, England) |
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| creator | Yi-Hua, Chen Yang, Jing Zi-Han, Lu Ke-Hua, Zhao Qi-Ying, Xie Sheng-Jiao, Yan |
| description | A novel protocol for the synthesis of highly functionalized benzo[b][1,5]diazocin-6(5H)-one derivatives (BDCOs, 4 and 5) from 2-aryl-1H-indoles and 1,1-enediamines was developed via a complex cascade of reactions including regioselective free radical oxidation, the 1,2-addition of imine, imine–enamine tautomerization, intramolecular cyclization, and ring expansion. The cascade reaction was enabled by refluxing a mixture of two substrates in the presence of di-tert-butyl peroxide (DTBP) as an oxidant and anhydrous CuI as a catalyst in toluene under argon protection. Consequently, a series of BDCOs (4 and 5) were synthesized with high regioselectivity in good yield. This protocol can be used for the synthesis of functionalized BDCOs via a one-pot oxidative annulation reaction rather than a multi-step reaction, which is suitable for both combinatorial and parallel syntheses of BDCOs. |
| doi_str_mv | 10.1039/d2cc06388c |
| format | Article |
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The cascade reaction was enabled by refluxing a mixture of two substrates in the presence of di-tert-butyl peroxide (DTBP) as an oxidant and anhydrous CuI as a catalyst in toluene under argon protection. Consequently, a series of BDCOs (4 and 5) were synthesized with high regioselectivity in good yield. This protocol can be used for the synthesis of functionalized BDCOs via a one-pot oxidative annulation reaction rather than a multi-step reaction, which is suitable for both combinatorial and parallel syntheses of BDCOs.</description><identifier>ISSN: 1359-7345</identifier><identifier>EISSN: 1364-548X</identifier><identifier>DOI: 10.1039/d2cc06388c</identifier><language>eng</language><publisher>Cambridge: Royal Society of Chemistry</publisher><subject>Argon ; Aromatic compounds ; Cascade chemical reactions ; Chemical reactions ; Chemical synthesis ; Combinatorial analysis ; Free radicals ; Indoles ; Oxidation ; Oxidizing agents ; Refluxing ; Regioselectivity ; Substrates ; Toluene</subject><ispartof>Chemical communications (Cambridge, England), 2023-01, Vol.59 (9), p.1217-1220</ispartof><rights>Copyright Royal Society of Chemistry 2023</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27901,27902</link.rule.ids></links><search><creatorcontrib>Yi-Hua, Chen</creatorcontrib><creatorcontrib>Yang, Jing</creatorcontrib><creatorcontrib>Zi-Han, Lu</creatorcontrib><creatorcontrib>Ke-Hua, Zhao</creatorcontrib><creatorcontrib>Qi-Ying, Xie</creatorcontrib><creatorcontrib>Sheng-Jiao, Yan</creatorcontrib><title>Synthesis of benzo[b][1,5]diazocin-6(5H)-one derivatives via the Cu-catalysed oxidative cyclization of 2-aryl-1H-indoles with 1,1-enediamines</title><title>Chemical communications (Cambridge, England)</title><description>A novel protocol for the synthesis of highly functionalized benzo[b][1,5]diazocin-6(5H)-one derivatives (BDCOs, 4 and 5) from 2-aryl-1H-indoles and 1,1-enediamines was developed via a complex cascade of reactions including regioselective free radical oxidation, the 1,2-addition of imine, imine–enamine tautomerization, intramolecular cyclization, and ring expansion. The cascade reaction was enabled by refluxing a mixture of two substrates in the presence of di-tert-butyl peroxide (DTBP) as an oxidant and anhydrous CuI as a catalyst in toluene under argon protection. Consequently, a series of BDCOs (4 and 5) were synthesized with high regioselectivity in good yield. This protocol can be used for the synthesis of functionalized BDCOs via a one-pot oxidative annulation reaction rather than a multi-step reaction, which is suitable for both combinatorial and parallel syntheses of BDCOs.</description><subject>Argon</subject><subject>Aromatic compounds</subject><subject>Cascade chemical reactions</subject><subject>Chemical reactions</subject><subject>Chemical synthesis</subject><subject>Combinatorial analysis</subject><subject>Free radicals</subject><subject>Indoles</subject><subject>Oxidation</subject><subject>Oxidizing agents</subject><subject>Refluxing</subject><subject>Regioselectivity</subject><subject>Substrates</subject><subject>Toluene</subject><issn>1359-7345</issn><issn>1364-548X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><recordid>eNpdj89KAzEQxhdRsFYvPkHAS4VGN5s_zR6lqBUEDyoIpZRNMqEp26Q2u9XtO_jOpurJucwH8_u-mcmyc5JfkZyW16bQOhdUSn2Q9QgVDHMm3w73mpd4RBk_zk5iXOapCJe97Ou5880CoosoWKTA78JUzaZkyGfGVbugncdiwCeXOHhABjZuWzVuCxFtXYWSE41brKumqrsIBoVPZ37mSHe6drukg98nF7jadDUmE-y8CXXyf7hmgciQYPCQVq2ch3iaHdmqjnD21_vZ693ty3iCH5_uH8Y3j3hdENFgLpg2QuW0kBKUogSMsJZJq2x6GRQoUeaEMGusGIlCg7aF1aZUJRWcKUb72eA3d70J7y3EZr5yUUNdVx5CG-fFSDDGiKQyoRf_0GVoNz5dt6dKXrKCM_oNlTN0Rg</recordid><startdate>20230126</startdate><enddate>20230126</enddate><creator>Yi-Hua, Chen</creator><creator>Yang, Jing</creator><creator>Zi-Han, Lu</creator><creator>Ke-Hua, Zhao</creator><creator>Qi-Ying, Xie</creator><creator>Sheng-Jiao, Yan</creator><general>Royal Society of Chemistry</general><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope><scope>7X8</scope></search><sort><creationdate>20230126</creationdate><title>Synthesis of benzo[b][1,5]diazocin-6(5H)-one derivatives via the Cu-catalysed oxidative cyclization of 2-aryl-1H-indoles with 1,1-enediamines</title><author>Yi-Hua, Chen ; Yang, Jing ; Zi-Han, Lu ; Ke-Hua, Zhao ; Qi-Ying, Xie ; Sheng-Jiao, Yan</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-p216t-564cd6b03288ebb31ed6ff48fbf364ebeb690114fdf6762cecf2fcd9b93654b43</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><topic>Argon</topic><topic>Aromatic compounds</topic><topic>Cascade chemical reactions</topic><topic>Chemical reactions</topic><topic>Chemical synthesis</topic><topic>Combinatorial analysis</topic><topic>Free radicals</topic><topic>Indoles</topic><topic>Oxidation</topic><topic>Oxidizing agents</topic><topic>Refluxing</topic><topic>Regioselectivity</topic><topic>Substrates</topic><topic>Toluene</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Yi-Hua, Chen</creatorcontrib><creatorcontrib>Yang, Jing</creatorcontrib><creatorcontrib>Zi-Han, Lu</creatorcontrib><creatorcontrib>Ke-Hua, Zhao</creatorcontrib><creatorcontrib>Qi-Ying, Xie</creatorcontrib><creatorcontrib>Sheng-Jiao, Yan</creatorcontrib><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><collection>MEDLINE - Academic</collection><jtitle>Chemical communications (Cambridge, England)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Yi-Hua, Chen</au><au>Yang, Jing</au><au>Zi-Han, Lu</au><au>Ke-Hua, Zhao</au><au>Qi-Ying, Xie</au><au>Sheng-Jiao, Yan</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of benzo[b][1,5]diazocin-6(5H)-one derivatives via the Cu-catalysed oxidative cyclization of 2-aryl-1H-indoles with 1,1-enediamines</atitle><jtitle>Chemical communications (Cambridge, England)</jtitle><date>2023-01-26</date><risdate>2023</risdate><volume>59</volume><issue>9</issue><spage>1217</spage><epage>1220</epage><pages>1217-1220</pages><issn>1359-7345</issn><eissn>1364-548X</eissn><abstract>A novel protocol for the synthesis of highly functionalized benzo[b][1,5]diazocin-6(5H)-one derivatives (BDCOs, 4 and 5) from 2-aryl-1H-indoles and 1,1-enediamines was developed via a complex cascade of reactions including regioselective free radical oxidation, the 1,2-addition of imine, imine–enamine tautomerization, intramolecular cyclization, and ring expansion. The cascade reaction was enabled by refluxing a mixture of two substrates in the presence of di-tert-butyl peroxide (DTBP) as an oxidant and anhydrous CuI as a catalyst in toluene under argon protection. Consequently, a series of BDCOs (4 and 5) were synthesized with high regioselectivity in good yield. This protocol can be used for the synthesis of functionalized BDCOs via a one-pot oxidative annulation reaction rather than a multi-step reaction, which is suitable for both combinatorial and parallel syntheses of BDCOs.</abstract><cop>Cambridge</cop><pub>Royal Society of Chemistry</pub><doi>10.1039/d2cc06388c</doi><tpages>4</tpages></addata></record> |
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| source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| subjects | Argon Aromatic compounds Cascade chemical reactions Chemical reactions Chemical synthesis Combinatorial analysis Free radicals Indoles Oxidation Oxidizing agents Refluxing Regioselectivity Substrates Toluene |
| title | Synthesis of benzo[b][1,5]diazocin-6(5H)-one derivatives via the Cu-catalysed oxidative cyclization of 2-aryl-1H-indoles with 1,1-enediamines |
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