Cascade Wolff Rearrangement and Double N‐Acylation: A Cyclization of α‐Diazoketones with 2‐aminopyridines or 3‐aminopyrazoles to Synthesize Fused Pyrimidinediones
A cascade Wolff rearrangement and double N‐acylation reaction has been developed for the synthesis of fused pyrimidinediones in one‐pot under air. These reactions were performed with α‐diazoketones and 2‐aminopyridines or 3‐aminopyrazoles under catalyst‐ and additive‐free conditions. The protocol av...
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| Veröffentlicht in: | Advanced synthesis & catalysis 2023-12, Vol.365 (23), p.4121-4126 |
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| container_issue | 23 |
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| container_title | Advanced synthesis & catalysis |
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| creator | Ren, Jun‐Jie Zhou, Jia‐Xin Song, Yanqin Zhang, An‐Xin Zhao, Lu‐Xin Zhao, Zun‐Yuan Zhu, Yan‐Ping Zhu, Wei |
| description | A cascade Wolff rearrangement and double N‐acylation reaction has been developed for the synthesis of fused pyrimidinediones in one‐pot under air. These reactions were performed with α‐diazoketones and 2‐aminopyridines or 3‐aminopyrazoles under catalyst‐ and additive‐free conditions. The protocol avoided traditional purification procedures, such as organic solvent extraction and column chromatography. The synthesis of biologically active molecules and gram‐scale experiment demonstrated the potential applications of this reaction. |
| doi_str_mv | 10.1002/adsc.202300773 |
| format | Article |
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These reactions were performed with α‐diazoketones and 2‐aminopyridines or 3‐aminopyrazoles under catalyst‐ and additive‐free conditions. The protocol avoided traditional purification procedures, such as organic solvent extraction and column chromatography. 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The synthesis of biologically active molecules and gram‐scale experiment demonstrated the potential applications of this reaction.</description><subject>Acylation</subject><subject>Cascade reaction</subject><subject>Catalyst- and additive-free</subject><subject>Chemical synthesis</subject><subject>Column chromatography</subject><subject>Double N-acylation</subject><subject>Fused pyrimidinediones</subject><subject>Solvent extraction</subject><subject>Wolff rearrangement</subject><issn>1615-4150</issn><issn>1615-4169</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2023</creationdate><recordtype>article</recordtype><recordid>eNqFkUtOwzAQhiMEEqWwZW2JdYsfeTjsqpQCUgWIglhGjh_UJY2LnapKVxyBe7DiIhyCk-C2qLBjNTO__m9mpD8IjhHsIgjxKROOdzHEBMIkITtBC8Uo6oQoTne3fQT3gwPnJhCihCZJK3jPmONMSPBoSqXAnWTWsupJTmVVA1YJ0DfzopTg-uv1rcebktXaVGegB7KGl3q5HoFR4PPDG_qaLc2zrE0lHVjoegywV9lUV2bWWC30SjcWkD-qJ0qv1gaMmqoeS6eXEgzmTgpw65npmhJ6tfIw2FOsdPLop7aDh8H5fXbZGd5cXGW9YYdjgkknJFQpzITiXCRRJKhiLGVpRIsoRTCKKcIxJhxGBZU4TNJCYR5iquIQorgglLSDk83emTUvc-nqfGLmtvInc0xTmuAQpci7uhsXt8Y5K1U-8-8y2-QI5qtA8lUg-TYQD6QbYKFL2fzjznv9UfbLfgN_q5cO</recordid><startdate>20231205</startdate><enddate>20231205</enddate><creator>Ren, Jun‐Jie</creator><creator>Zhou, Jia‐Xin</creator><creator>Song, Yanqin</creator><creator>Zhang, An‐Xin</creator><creator>Zhao, Lu‐Xin</creator><creator>Zhao, Zun‐Yuan</creator><creator>Zhu, Yan‐Ping</creator><creator>Zhu, Wei</creator><general>Wiley Subscription Services, Inc</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7U5</scope><scope>8FD</scope><scope>L7M</scope><orcidid>https://orcid.org/0000-0003-1666-1850</orcidid></search><sort><creationdate>20231205</creationdate><title>Cascade Wolff Rearrangement and Double N‐Acylation: A Cyclization of α‐Diazoketones with 2‐aminopyridines or 3‐aminopyrazoles to Synthesize Fused Pyrimidinediones</title><author>Ren, Jun‐Jie ; Zhou, Jia‐Xin ; Song, Yanqin ; Zhang, An‐Xin ; Zhao, Lu‐Xin ; Zhao, Zun‐Yuan ; Zhu, Yan‐Ping ; Zhu, Wei</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c2323-438ff2adfccd755d8faa9a958b591056812623c05b8e2479bf2c428f64016b383</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2023</creationdate><topic>Acylation</topic><topic>Cascade reaction</topic><topic>Catalyst- and additive-free</topic><topic>Chemical synthesis</topic><topic>Column chromatography</topic><topic>Double N-acylation</topic><topic>Fused pyrimidinediones</topic><topic>Solvent extraction</topic><topic>Wolff rearrangement</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Ren, Jun‐Jie</creatorcontrib><creatorcontrib>Zhou, Jia‐Xin</creatorcontrib><creatorcontrib>Song, Yanqin</creatorcontrib><creatorcontrib>Zhang, An‐Xin</creatorcontrib><creatorcontrib>Zhao, Lu‐Xin</creatorcontrib><creatorcontrib>Zhao, Zun‐Yuan</creatorcontrib><creatorcontrib>Zhu, Yan‐Ping</creatorcontrib><creatorcontrib>Zhu, Wei</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>Ren, Jun‐Jie</au><au>Zhou, Jia‐Xin</au><au>Song, Yanqin</au><au>Zhang, An‐Xin</au><au>Zhao, Lu‐Xin</au><au>Zhao, Zun‐Yuan</au><au>Zhu, Yan‐Ping</au><au>Zhu, Wei</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Cascade Wolff Rearrangement and Double N‐Acylation: A Cyclization of α‐Diazoketones with 2‐aminopyridines or 3‐aminopyrazoles to Synthesize Fused Pyrimidinediones</atitle><jtitle>Advanced synthesis & catalysis</jtitle><date>2023-12-05</date><risdate>2023</risdate><volume>365</volume><issue>23</issue><spage>4121</spage><epage>4126</epage><pages>4121-4126</pages><issn>1615-4150</issn><eissn>1615-4169</eissn><abstract>A cascade Wolff rearrangement and double N‐acylation reaction has been developed for the synthesis of fused pyrimidinediones in one‐pot under air. 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| ispartof | Advanced synthesis & catalysis, 2023-12, Vol.365 (23), p.4121-4126 |
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| language | eng |
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| source | Wiley Online Library Journals Frontfile Complete |
| subjects | Acylation Cascade reaction Catalyst- and additive-free Chemical synthesis Column chromatography Double N-acylation Fused pyrimidinediones Solvent extraction Wolff rearrangement |
| title | Cascade Wolff Rearrangement and Double N‐Acylation: A Cyclization of α‐Diazoketones with 2‐aminopyridines or 3‐aminopyrazoles to Synthesize Fused Pyrimidinediones |
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