Synthesis of unsymmetrical urea derivatives one-pot sequential three-component reactions of cyclic 2-diazo-1,3-diketones, carbodiimides, and 1,2-dihaloethanes
A novel and efficient multicomponent reaction of cyclic 2-diazo-1,3-diketones, carbodiimides, and 1,2-dihaloethanes has been developed, and it leads to unsymmetrical urea derivatives with good yields in a single operation. This transformation involves the cascade formation of C-X (X = Cl, Br, I), C-...
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| Veröffentlicht in: | Organic & biomolecular chemistry 2020-06, Vol.18 (22), p.4178-4182 |
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| container_title | Organic & biomolecular chemistry |
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| creator | He, Xinwei Yang, Cheng Wu, Yinsong Xie, Mengqing Li, Ruxue Duan, Jiahui Shang, Yongjia |
| description | A novel and efficient multicomponent reaction of cyclic 2-diazo-1,3-diketones, carbodiimides, and 1,2-dihaloethanes has been developed, and it leads to unsymmetrical urea derivatives with good yields in a single operation. This transformation involves the cascade formation of C-X (X = Cl, Br, I), C-N and C&z.dbd;O bonds through halogenation, nucleophilic addition, ring-opening, and enol-ketone tautomerization processes. This protocol is step- and atom-economical; 1,2-dihaloethane was used as an easily available halogenated reagent, and it is amenable to different functional groups.
An effective and operationally simple one-pot strategy has been developed for the synthesis of unsymmetrical urea derivatives
via
sequential three-component reactions of cyclic 2-dizao-1,3-diketones with carbodiimides and 1,2-dihaloethane. |
| doi_str_mv | 10.1039/d0ob00683a |
| format | Article |
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An effective and operationally simple one-pot strategy has been developed for the synthesis of unsymmetrical urea derivatives
via
sequential three-component reactions of cyclic 2-dizao-1,3-diketones with carbodiimides and 1,2-dihaloethane.</description><identifier>ISSN: 1477-0520</identifier><identifier>EISSN: 1477-0539</identifier><identifier>DOI: 10.1039/d0ob00683a</identifier><language>eng</language><ispartof>Organic & biomolecular chemistry, 2020-06, Vol.18 (22), p.4178-4182</ispartof><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>314,776,780,27903,27904</link.rule.ids></links><search><creatorcontrib>He, Xinwei</creatorcontrib><creatorcontrib>Yang, Cheng</creatorcontrib><creatorcontrib>Wu, Yinsong</creatorcontrib><creatorcontrib>Xie, Mengqing</creatorcontrib><creatorcontrib>Li, Ruxue</creatorcontrib><creatorcontrib>Duan, Jiahui</creatorcontrib><creatorcontrib>Shang, Yongjia</creatorcontrib><title>Synthesis of unsymmetrical urea derivatives one-pot sequential three-component reactions of cyclic 2-diazo-1,3-diketones, carbodiimides, and 1,2-dihaloethanes</title><title>Organic & biomolecular chemistry</title><description>A novel and efficient multicomponent reaction of cyclic 2-diazo-1,3-diketones, carbodiimides, and 1,2-dihaloethanes has been developed, and it leads to unsymmetrical urea derivatives with good yields in a single operation. This transformation involves the cascade formation of C-X (X = Cl, Br, I), C-N and C&z.dbd;O bonds through halogenation, nucleophilic addition, ring-opening, and enol-ketone tautomerization processes. This protocol is step- and atom-economical; 1,2-dihaloethane was used as an easily available halogenated reagent, and it is amenable to different functional groups.
An effective and operationally simple one-pot strategy has been developed for the synthesis of unsymmetrical urea derivatives
via
sequential three-component reactions of cyclic 2-dizao-1,3-diketones with carbodiimides and 1,2-dihaloethane.</description><issn>1477-0520</issn><issn>1477-0539</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2020</creationdate><recordtype>article</recordtype><sourceid/><recordid>eNqFj0FLxDAQhYMouK5evAvx3miyWbf2LIp3vZfZZEpHm6Qm6UL9Mf5WsyJ609N7j_fNg2HsXMkrJXVzbWXYSrm51XDAFmpd10Le6Obwx6_kMTtJ6UVK1dSb9YJ9PM0-95go8dDxyafZOcyRDAx8igjcYqQdZNphITyKMWSe8G1Cn6kwuY-IwgQ3ltJnXk5MpuC_5sxsBjJ8JSzBexCq0sW9Yi5oqriBuA2WyJHdR_CWq2rP9jAEzD0U6pQddTAkPPvWJbt4uH--exQxmXaM5CDO7e_Tesku_-rb0Xb6v41PlXRpJQ</recordid><startdate>20200610</startdate><enddate>20200610</enddate><creator>He, Xinwei</creator><creator>Yang, Cheng</creator><creator>Wu, Yinsong</creator><creator>Xie, Mengqing</creator><creator>Li, Ruxue</creator><creator>Duan, Jiahui</creator><creator>Shang, Yongjia</creator><scope/></search><sort><creationdate>20200610</creationdate><title>Synthesis of unsymmetrical urea derivatives one-pot sequential three-component reactions of cyclic 2-diazo-1,3-diketones, carbodiimides, and 1,2-dihaloethanes</title><author>He, Xinwei ; Yang, Cheng ; Wu, Yinsong ; Xie, Mengqing ; Li, Ruxue ; Duan, Jiahui ; Shang, Yongjia</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-rsc_primary_d0ob00683a3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2020</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>He, Xinwei</creatorcontrib><creatorcontrib>Yang, Cheng</creatorcontrib><creatorcontrib>Wu, Yinsong</creatorcontrib><creatorcontrib>Xie, Mengqing</creatorcontrib><creatorcontrib>Li, Ruxue</creatorcontrib><creatorcontrib>Duan, Jiahui</creatorcontrib><creatorcontrib>Shang, Yongjia</creatorcontrib><jtitle>Organic & biomolecular chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>He, Xinwei</au><au>Yang, Cheng</au><au>Wu, Yinsong</au><au>Xie, Mengqing</au><au>Li, Ruxue</au><au>Duan, Jiahui</au><au>Shang, Yongjia</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of unsymmetrical urea derivatives one-pot sequential three-component reactions of cyclic 2-diazo-1,3-diketones, carbodiimides, and 1,2-dihaloethanes</atitle><jtitle>Organic & biomolecular chemistry</jtitle><date>2020-06-10</date><risdate>2020</risdate><volume>18</volume><issue>22</issue><spage>4178</spage><epage>4182</epage><pages>4178-4182</pages><issn>1477-0520</issn><eissn>1477-0539</eissn><abstract>A novel and efficient multicomponent reaction of cyclic 2-diazo-1,3-diketones, carbodiimides, and 1,2-dihaloethanes has been developed, and it leads to unsymmetrical urea derivatives with good yields in a single operation. This transformation involves the cascade formation of C-X (X = Cl, Br, I), C-N and C&z.dbd;O bonds through halogenation, nucleophilic addition, ring-opening, and enol-ketone tautomerization processes. This protocol is step- and atom-economical; 1,2-dihaloethane was used as an easily available halogenated reagent, and it is amenable to different functional groups.
An effective and operationally simple one-pot strategy has been developed for the synthesis of unsymmetrical urea derivatives
via
sequential three-component reactions of cyclic 2-dizao-1,3-diketones with carbodiimides and 1,2-dihaloethane.</abstract><doi>10.1039/d0ob00683a</doi><tpages>5</tpages></addata></record> |
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| source | Alma/SFX Local Collection; Royal Society of Chemistry E-Journals |
| title | Synthesis of unsymmetrical urea derivatives one-pot sequential three-component reactions of cyclic 2-diazo-1,3-diketones, carbodiimides, and 1,2-dihaloethanes |
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