Visible‐Light‐Induced Diastereoselective Cascade Cyclization to Construct Polycyclic Spiroindolines
We herein reported, a visible‐light‐induced K2S2O8 mediated cascade reaction of 3‐(2‐isocyanoethyl)indoles with α‐oxocarboxylic acids leading to diastereoselective synthesis of polycyclic spiroindolines bearing an N‐formyl unit derivative utilising the alkali metal salt K2S2O8 as a mediator under mi...
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| Veröffentlicht in: | Advanced synthesis & catalysis 2024-08, Vol.366 (15), p.3303-3309 |
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| container_issue | 15 |
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| container_title | Advanced synthesis & catalysis |
| container_volume | 366 |
| creator | Ranga Rao, Vadithya Shiva Prasad, Vadla Ravi, Dharavath Anil Kumar, Chelukalapally Kumar Nechipadappu, Sunil ReddyAdiyala, Praveen |
| description | We herein reported, a visible‐light‐induced K2S2O8 mediated cascade reaction of 3‐(2‐isocyanoethyl)indoles with α‐oxocarboxylic acids leading to diastereoselective synthesis of polycyclic spiroindolines bearing an N‐formyl unit derivative utilising the alkali metal salt K2S2O8 as a mediator under mild reaction conditions. This study offers an illustration of α‐oxocarboxylic acids and 3‐(2‐isocyanoethyl)indoles‐based reactions as it shows the involvement of glyoxolate ions without decarboxylation to access polycyclic spiroindolines bearing an N‐formyl unit analogue. The batch process can be extended to a continuous flow system using a glass tube loaded with K2S2O8 placed between the PFA capillary reactor, which can greatly advance the reaction efficiency and can even be promoted to gram‐scale synthesis. |
| doi_str_mv | 10.1002/adsc.202400406 |
| format | Article |
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This study offers an illustration of α‐oxocarboxylic acids and 3‐(2‐isocyanoethyl)indoles‐based reactions as it shows the involvement of glyoxolate ions without decarboxylation to access polycyclic spiroindolines bearing an N‐formyl unit analogue. The batch process can be extended to a continuous flow system using a glass tube loaded with K2S2O8 placed between the PFA capillary reactor, which can greatly advance the reaction efficiency and can even be promoted to gram‐scale synthesis.</description><identifier>ISSN: 1615-4150</identifier><identifier>EISSN: 1615-4169</identifier><identifier>DOI: 10.1002/adsc.202400406</identifier><language>eng</language><publisher>Heidelberg: Wiley Subscription Services, Inc</publisher><subject>3-(2-isocyanoethyl)indoles ; alkali metal salt K2S2O8 ; Alkali metals ; Capillary flow ; Capillary tubes ; Cascade chemical reactions ; Chemical synthesis ; Continuous flow ; Decarboxylation ; Indoles ; PFA (Perfluoroalkoxy alkane) capillary micro reactor ; polycyclic spiroindolines ; Potassium persulfate ; Stereoselectivity ; Visible-light ; α-oxocarboxylic acids</subject><ispartof>Advanced synthesis & catalysis, 2024-08, Vol.366 (15), p.3303-3309</ispartof><rights>2024 Wiley-VCH GmbH</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><cites>FETCH-LOGICAL-c2026-7f5ce4decb1be2a5b190ebdd9c1461f5cfcd6307204db604131ea442d1b4d5763</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fadsc.202400406$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fadsc.202400406$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids></links><search><creatorcontrib>Ranga Rao, Vadithya</creatorcontrib><creatorcontrib>Shiva Prasad, Vadla</creatorcontrib><creatorcontrib>Ravi, Dharavath</creatorcontrib><creatorcontrib>Anil Kumar, Chelukalapally</creatorcontrib><creatorcontrib>Kumar Nechipadappu, Sunil</creatorcontrib><creatorcontrib>ReddyAdiyala, Praveen</creatorcontrib><title>Visible‐Light‐Induced Diastereoselective Cascade Cyclization to Construct Polycyclic Spiroindolines</title><title>Advanced synthesis & catalysis</title><description>We herein reported, a visible‐light‐induced K2S2O8 mediated cascade reaction of 3‐(2‐isocyanoethyl)indoles with α‐oxocarboxylic acids leading to diastereoselective synthesis of polycyclic spiroindolines bearing an N‐formyl unit derivative utilising the alkali metal salt K2S2O8 as a mediator under mild reaction conditions. This study offers an illustration of α‐oxocarboxylic acids and 3‐(2‐isocyanoethyl)indoles‐based reactions as it shows the involvement of glyoxolate ions without decarboxylation to access polycyclic spiroindolines bearing an N‐formyl unit analogue. The batch process can be extended to a continuous flow system using a glass tube loaded with K2S2O8 placed between the PFA capillary reactor, which can greatly advance the reaction efficiency and can even be promoted to gram‐scale synthesis.</description><subject>3-(2-isocyanoethyl)indoles</subject><subject>alkali metal salt K2S2O8</subject><subject>Alkali metals</subject><subject>Capillary flow</subject><subject>Capillary tubes</subject><subject>Cascade chemical reactions</subject><subject>Chemical synthesis</subject><subject>Continuous flow</subject><subject>Decarboxylation</subject><subject>Indoles</subject><subject>PFA (Perfluoroalkoxy alkane) capillary micro reactor</subject><subject>polycyclic spiroindolines</subject><subject>Potassium persulfate</subject><subject>Stereoselectivity</subject><subject>Visible-light</subject><subject>α-oxocarboxylic acids</subject><issn>1615-4150</issn><issn>1615-4169</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2024</creationdate><recordtype>article</recordtype><recordid>eNqFkM1OwzAQhC0EEqVw5RyJc8o6cRxyrFJ-KlUCqcDVcuxNcRXiYjugcOIReEaehFRFcOQ0K803u6sh5JTChAIk51J7NUkgYQAM-B4ZUU6zmFFe7P_OGRySI-_XADS_yPMRWT0ab6oGvz4-F2b1FAadt7pTqKOZkT6gQ-uxQRXMK0al9ErqQXvVmHcZjG2jYKPStj64ToXozja92poqWm6Ms6bVtjEt-mNyUMvG48mPjsnD1eV9eRMvbq_n5XQRq-FzHud1ppBpVBWtMJFZRQvASutCUcbpYNZK8xTyBJiuODCaUpSMJZpWTGc5T8fkbLd34-xLhz6Ite1cO5wUKRQsT7MkLQZqsqOUs947rMXGmWfpekFBbMsU2zLFb5lDoNgF3kyD_T-0mM6W5V_2GztXfNY</recordid><startdate>20240806</startdate><enddate>20240806</enddate><creator>Ranga Rao, Vadithya</creator><creator>Shiva Prasad, Vadla</creator><creator>Ravi, Dharavath</creator><creator>Anil Kumar, Chelukalapally</creator><creator>Kumar Nechipadappu, Sunil</creator><creator>ReddyAdiyala, Praveen</creator><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7U5</scope><scope>8FD</scope><scope>L7M</scope></search><sort><creationdate>20240806</creationdate><title>Visible‐Light‐Induced Diastereoselective Cascade Cyclization to Construct Polycyclic Spiroindolines</title><author>Ranga Rao, Vadithya ; Shiva Prasad, Vadla ; Ravi, Dharavath ; Anil Kumar, Chelukalapally ; Kumar Nechipadappu, Sunil ; ReddyAdiyala, Praveen</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c2026-7f5ce4decb1be2a5b190ebdd9c1461f5cfcd6307204db604131ea442d1b4d5763</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2024</creationdate><topic>3-(2-isocyanoethyl)indoles</topic><topic>alkali metal salt K2S2O8</topic><topic>Alkali metals</topic><topic>Capillary flow</topic><topic>Capillary tubes</topic><topic>Cascade chemical reactions</topic><topic>Chemical synthesis</topic><topic>Continuous flow</topic><topic>Decarboxylation</topic><topic>Indoles</topic><topic>PFA (Perfluoroalkoxy alkane) capillary micro reactor</topic><topic>polycyclic spiroindolines</topic><topic>Potassium persulfate</topic><topic>Stereoselectivity</topic><topic>Visible-light</topic><topic>α-oxocarboxylic acids</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ranga Rao, Vadithya</creatorcontrib><creatorcontrib>Shiva Prasad, Vadla</creatorcontrib><creatorcontrib>Ravi, Dharavath</creatorcontrib><creatorcontrib>Anil Kumar, Chelukalapally</creatorcontrib><creatorcontrib>Kumar Nechipadappu, Sunil</creatorcontrib><creatorcontrib>ReddyAdiyala, Praveen</creatorcontrib><collection>CrossRef</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>Technology Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Advanced synthesis & catalysis</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Ranga Rao, Vadithya</au><au>Shiva Prasad, Vadla</au><au>Ravi, Dharavath</au><au>Anil Kumar, Chelukalapally</au><au>Kumar Nechipadappu, Sunil</au><au>ReddyAdiyala, Praveen</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Visible‐Light‐Induced Diastereoselective Cascade Cyclization to Construct Polycyclic Spiroindolines</atitle><jtitle>Advanced synthesis & catalysis</jtitle><date>2024-08-06</date><risdate>2024</risdate><volume>366</volume><issue>15</issue><spage>3303</spage><epage>3309</epage><pages>3303-3309</pages><issn>1615-4150</issn><eissn>1615-4169</eissn><abstract>We herein reported, a visible‐light‐induced K2S2O8 mediated cascade reaction of 3‐(2‐isocyanoethyl)indoles with α‐oxocarboxylic acids leading to diastereoselective synthesis of polycyclic spiroindolines bearing an N‐formyl unit derivative utilising the alkali metal salt K2S2O8 as a mediator under mild reaction conditions. This study offers an illustration of α‐oxocarboxylic acids and 3‐(2‐isocyanoethyl)indoles‐based reactions as it shows the involvement of glyoxolate ions without decarboxylation to access polycyclic spiroindolines bearing an N‐formyl unit analogue. The batch process can be extended to a continuous flow system using a glass tube loaded with K2S2O8 placed between the PFA capillary reactor, which can greatly advance the reaction efficiency and can even be promoted to gram‐scale synthesis.</abstract><cop>Heidelberg</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/adsc.202400406</doi><tpages>7</tpages></addata></record> |
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| subjects | 3-(2-isocyanoethyl)indoles alkali metal salt K2S2O8 Alkali metals Capillary flow Capillary tubes Cascade chemical reactions Chemical synthesis Continuous flow Decarboxylation Indoles PFA (Perfluoroalkoxy alkane) capillary micro reactor polycyclic spiroindolines Potassium persulfate Stereoselectivity Visible-light α-oxocarboxylic acids |
| title | Visible‐Light‐Induced Diastereoselective Cascade Cyclization to Construct Polycyclic Spiroindolines |
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