Synthesis of 3‐(Phenylcarbonyl)‐1H‐indazole Derivatives through Intramolecular Cyclization under Mild Conditions
The synthesis of 3‐(phenylcarbonyl)‐1H‐indazole derivatives via the intramolecular cyclization of triazene derivatives substituted by a 2‐(phenylethynyl)phenyl group at the position 3 was developed. The azonium salt, the key intermediate in the reaction, was prepared under mild conditions from trime...
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| Veröffentlicht in: | Asian journal of organic chemistry 2022-11, Vol.11 (11), p.n/a |
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| container_title | Asian journal of organic chemistry |
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| creator | Kuroyanagi, Sota Kikuchi, Shumpei Sumikoshi, Shunsuke Uwano, Mizuho Chiba, Takayuki Yamakado, Ryohei Okada, Shuji |
| description | The synthesis of 3‐(phenylcarbonyl)‐1H‐indazole derivatives via the intramolecular cyclization of triazene derivatives substituted by a 2‐(phenylethynyl)phenyl group at the position 3 was developed. The azonium salt, the key intermediate in the reaction, was prepared under mild conditions from trimethylsilyl iodide (TMSI) obtained from an in situ mixture of trimethylsilyl chloride (TMSCl) and sodium iodide (NaI). The obtained 3‐(phenylcarbonyl)‐1H‐indazole derivatives exhibited interesting optical properties including phosphorescence, which was verified by theoretical calculations.
Intramolecular cyclization of phenylethynyl‐substituted triazene derivatives was developed for the preparation of 3‐(phenylcarbonyl)‐1H‐indazole derivatives. The azonium salt, the key intermediate in the reaction, was prepared under mild conditions from trimethylsilyl iodide obtained from an in‐situ mixture of trimethylsilyl chloride and sodium iodide. The obtained 3‐(phenylcarbonyl)‐1H‐indazole derivatives exhibited interesting optical properties including phosphorescence. |
| doi_str_mv | 10.1002/ajoc.202200423 |
| format | Article |
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Intramolecular cyclization of phenylethynyl‐substituted triazene derivatives was developed for the preparation of 3‐(phenylcarbonyl)‐1H‐indazole derivatives. The azonium salt, the key intermediate in the reaction, was prepared under mild conditions from trimethylsilyl iodide obtained from an in‐situ mixture of trimethylsilyl chloride and sodium iodide. The obtained 3‐(phenylcarbonyl)‐1H‐indazole derivatives exhibited interesting optical properties including phosphorescence.</description><identifier>ISSN: 2193-5807</identifier><identifier>EISSN: 2193-5815</identifier><identifier>DOI: 10.1002/ajoc.202200423</identifier><language>eng</language><publisher>Weinheim: Wiley Subscription Services, Inc</publisher><subject>azonium ; indazole ; intramolecular cyclization ; Optical properties ; Organic chemistry ; Phosphorescence ; Synthesis ; transition metals free reaction</subject><ispartof>Asian journal of organic chemistry, 2022-11, Vol.11 (11), p.n/a</ispartof><rights>2022 Wiley‐VCH GmbH</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><orcidid>0000-0002-6893-7874 ; 0000-0003-4085-9226 ; 0000-0001-9519-6648</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%2Fajoc.202200423$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fajoc.202200423$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,780,784,1416,27923,27924,45573,45574</link.rule.ids></links><search><creatorcontrib>Kuroyanagi, Sota</creatorcontrib><creatorcontrib>Kikuchi, Shumpei</creatorcontrib><creatorcontrib>Sumikoshi, Shunsuke</creatorcontrib><creatorcontrib>Uwano, Mizuho</creatorcontrib><creatorcontrib>Chiba, Takayuki</creatorcontrib><creatorcontrib>Yamakado, Ryohei</creatorcontrib><creatorcontrib>Okada, Shuji</creatorcontrib><title>Synthesis of 3‐(Phenylcarbonyl)‐1H‐indazole Derivatives through Intramolecular Cyclization under Mild Conditions</title><title>Asian journal of organic chemistry</title><description>The synthesis of 3‐(phenylcarbonyl)‐1H‐indazole derivatives via the intramolecular cyclization of triazene derivatives substituted by a 2‐(phenylethynyl)phenyl group at the position 3 was developed. The azonium salt, the key intermediate in the reaction, was prepared under mild conditions from trimethylsilyl iodide (TMSI) obtained from an in situ mixture of trimethylsilyl chloride (TMSCl) and sodium iodide (NaI). The obtained 3‐(phenylcarbonyl)‐1H‐indazole derivatives exhibited interesting optical properties including phosphorescence, which was verified by theoretical calculations.
Intramolecular cyclization of phenylethynyl‐substituted triazene derivatives was developed for the preparation of 3‐(phenylcarbonyl)‐1H‐indazole derivatives. The azonium salt, the key intermediate in the reaction, was prepared under mild conditions from trimethylsilyl iodide obtained from an in‐situ mixture of trimethylsilyl chloride and sodium iodide. The obtained 3‐(phenylcarbonyl)‐1H‐indazole derivatives exhibited interesting optical properties including phosphorescence.</description><subject>azonium</subject><subject>indazole</subject><subject>intramolecular cyclization</subject><subject>Optical properties</subject><subject>Organic chemistry</subject><subject>Phosphorescence</subject><subject>Synthesis</subject><subject>transition metals free reaction</subject><issn>2193-5807</issn><issn>2193-5815</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2022</creationdate><recordtype>article</recordtype><sourceid/><recordid>eNo9UMtOwzAQjBBIVKVXzpa4wKHFjziJj1V4tKioSMDZsh2HOErj4iRF6YlP4Bv5EhwVdQ87u7Oj3dUEwSWCMwQhvhWlVTMMMYYwxOQkGGHEyJQmiJ4eaxifB5OmKaGPOGYIs1Gwe-3rttCNaYDNAfn9_rl-KXTdV0o4aT3eeAotfDJ1Jva20uBOO7MTrdnpBrSFs91HAZZ168TGT1VXCQfSXlVm7zW2Bl2daQeeTZWB1NaZGcjmIjjLRdXoyT-Og_eH-7d0MV2tH5fpfDUtMfM_Y4GhzENNExJGkkYUEqUlUSSWkqlcw4RChHAo85xRqmKSZImEeZxkiOFIITIOrg57t85-drppeWk7V_uTHMckpgmNokHFDqovU-meb53ZCNdzBPngLR-85Udv-fxpnR478gfccnPY</recordid><startdate>202211</startdate><enddate>202211</enddate><creator>Kuroyanagi, Sota</creator><creator>Kikuchi, Shumpei</creator><creator>Sumikoshi, Shunsuke</creator><creator>Uwano, Mizuho</creator><creator>Chiba, Takayuki</creator><creator>Yamakado, Ryohei</creator><creator>Okada, Shuji</creator><general>Wiley Subscription Services, Inc</general><scope/><orcidid>https://orcid.org/0000-0002-6893-7874</orcidid><orcidid>https://orcid.org/0000-0003-4085-9226</orcidid><orcidid>https://orcid.org/0000-0001-9519-6648</orcidid></search><sort><creationdate>202211</creationdate><title>Synthesis of 3‐(Phenylcarbonyl)‐1H‐indazole Derivatives through Intramolecular Cyclization under Mild Conditions</title><author>Kuroyanagi, Sota ; Kikuchi, Shumpei ; Sumikoshi, Shunsuke ; Uwano, Mizuho ; Chiba, Takayuki ; Yamakado, Ryohei ; Okada, Shuji</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-j2993-2a20bf4e58346b56503ceb3c37bb9cfe08501124bff955c738d8b0f78d1926c13</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2022</creationdate><topic>azonium</topic><topic>indazole</topic><topic>intramolecular cyclization</topic><topic>Optical properties</topic><topic>Organic chemistry</topic><topic>Phosphorescence</topic><topic>Synthesis</topic><topic>transition metals free reaction</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kuroyanagi, Sota</creatorcontrib><creatorcontrib>Kikuchi, Shumpei</creatorcontrib><creatorcontrib>Sumikoshi, Shunsuke</creatorcontrib><creatorcontrib>Uwano, Mizuho</creatorcontrib><creatorcontrib>Chiba, Takayuki</creatorcontrib><creatorcontrib>Yamakado, Ryohei</creatorcontrib><creatorcontrib>Okada, Shuji</creatorcontrib><jtitle>Asian journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kuroyanagi, Sota</au><au>Kikuchi, Shumpei</au><au>Sumikoshi, Shunsuke</au><au>Uwano, Mizuho</au><au>Chiba, Takayuki</au><au>Yamakado, Ryohei</au><au>Okada, Shuji</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of 3‐(Phenylcarbonyl)‐1H‐indazole Derivatives through Intramolecular Cyclization under Mild Conditions</atitle><jtitle>Asian journal of organic chemistry</jtitle><date>2022-11</date><risdate>2022</risdate><volume>11</volume><issue>11</issue><epage>n/a</epage><issn>2193-5807</issn><eissn>2193-5815</eissn><abstract>The synthesis of 3‐(phenylcarbonyl)‐1H‐indazole derivatives via the intramolecular cyclization of triazene derivatives substituted by a 2‐(phenylethynyl)phenyl group at the position 3 was developed. The azonium salt, the key intermediate in the reaction, was prepared under mild conditions from trimethylsilyl iodide (TMSI) obtained from an in situ mixture of trimethylsilyl chloride (TMSCl) and sodium iodide (NaI). The obtained 3‐(phenylcarbonyl)‐1H‐indazole derivatives exhibited interesting optical properties including phosphorescence, which was verified by theoretical calculations.
Intramolecular cyclization of phenylethynyl‐substituted triazene derivatives was developed for the preparation of 3‐(phenylcarbonyl)‐1H‐indazole derivatives. The azonium salt, the key intermediate in the reaction, was prepared under mild conditions from trimethylsilyl iodide obtained from an in‐situ mixture of trimethylsilyl chloride and sodium iodide. The obtained 3‐(phenylcarbonyl)‐1H‐indazole derivatives exhibited interesting optical properties including phosphorescence.</abstract><cop>Weinheim</cop><pub>Wiley Subscription Services, Inc</pub><doi>10.1002/ajoc.202200423</doi><tpages>5</tpages><orcidid>https://orcid.org/0000-0002-6893-7874</orcidid><orcidid>https://orcid.org/0000-0003-4085-9226</orcidid><orcidid>https://orcid.org/0000-0001-9519-6648</orcidid></addata></record> |
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| subjects | azonium indazole intramolecular cyclization Optical properties Organic chemistry Phosphorescence Synthesis transition metals free reaction |
| title | Synthesis of 3‐(Phenylcarbonyl)‐1H‐indazole Derivatives through Intramolecular Cyclization under Mild Conditions |
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