Copper-Catalyzed Cascade Cyclization Reaction of 2-Haloaryltriazenes and Sodium Azide: Selective Synthesis of 2 H-Benzotriazoles in Water
A new approach to the synthesis of 2 H‐benzotriazoles is described. This strategy is based on the copper‐catalyzed CN coupling of 2‐haloaryltriazenes or 2‐haloazo compounds with sodium azide and the intramolecular addition of nitrene to NN bonds. This approach allows the synthesis of various N‐ami...
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| Veröffentlicht in: | Chemistry : a European journal 2014-02, Vol.20 (7), p.1825-1828 |
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| container_title | Chemistry : a European journal |
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| creator | Shang, Xiaobo Zhao, Shixian Chen, Wanzhi Chen, Chao Qiu, Huayu |
| description | A new approach to the synthesis of 2 H‐benzotriazoles is described. This strategy is based on the copper‐catalyzed CN coupling of 2‐haloaryltriazenes or 2‐haloazo compounds with sodium azide and the intramolecular addition of nitrene to NN bonds. This approach allows the synthesis of various N‐amino‐ and N‐aryl‐2 H‐benzotriazoles in water, in good to excellent yields. The procedure is simple and the starting materials and catalyst are easily available, offering a practical and convenient synthetic route to 2‐substituted benzotriazoles.
A new approach to the synthesis of 2 H‐benzotriazoles is described. This strategy is based on the copper‐catalyzed CN coupling of 2‐haloaryltriazenes or 2‐haloazo compounds with sodium azide and the intramolecular addition of a nitrene species to NN bonds (see scheme; TMEDA=N,N,N′,N′‐tetramethylethylenediamine; CTAB=hexadecyltrimethylammonium bromide). This approach allows the synthesis of various N‐amino‐ and N‐aryl‐2 H‐benzotriazoles in water, in good to excellent yields. |
| doi_str_mv | 10.1002/chem.201303712 |
| format | Article |
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A new approach to the synthesis of 2 H‐benzotriazoles is described. This strategy is based on the copper‐catalyzed CN coupling of 2‐haloaryltriazenes or 2‐haloazo compounds with sodium azide and the intramolecular addition of a nitrene species to NN bonds (see scheme; TMEDA=N,N,N′,N′‐tetramethylethylenediamine; CTAB=hexadecyltrimethylammonium bromide). This approach allows the synthesis of various N‐amino‐ and N‐aryl‐2 H‐benzotriazoles in water, in good to excellent yields.</description><identifier>ISSN: 0947-6539</identifier><identifier>EISSN: 1521-3765</identifier><identifier>DOI: 10.1002/chem.201303712</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag</publisher><subject>benzotriazoles ; cascade cyclizations ; sodium azide ; water</subject><ispartof>Chemistry : a European journal, 2014-02, Vol.20 (7), p.1825-1828</ispartof><rights>Copyright © 2014 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3452-3856321d09dc374d531458ef411df9d2d522d0fe3d67c958051678337b9691ff3</citedby><cites>FETCH-LOGICAL-c3452-3856321d09dc374d531458ef411df9d2d522d0fe3d67c958051678337b9691ff3</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%2Fchem.201303712$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fchem.201303712$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27903,27904,45553,45554</link.rule.ids></links><search><creatorcontrib>Shang, Xiaobo</creatorcontrib><creatorcontrib>Zhao, Shixian</creatorcontrib><creatorcontrib>Chen, Wanzhi</creatorcontrib><creatorcontrib>Chen, Chao</creatorcontrib><creatorcontrib>Qiu, Huayu</creatorcontrib><title>Copper-Catalyzed Cascade Cyclization Reaction of 2-Haloaryltriazenes and Sodium Azide: Selective Synthesis of 2 H-Benzotriazoles in Water</title><title>Chemistry : a European journal</title><addtitle>Chem. Eur. J</addtitle><description>A new approach to the synthesis of 2 H‐benzotriazoles is described. This strategy is based on the copper‐catalyzed CN coupling of 2‐haloaryltriazenes or 2‐haloazo compounds with sodium azide and the intramolecular addition of nitrene to NN bonds. This approach allows the synthesis of various N‐amino‐ and N‐aryl‐2 H‐benzotriazoles in water, in good to excellent yields. The procedure is simple and the starting materials and catalyst are easily available, offering a practical and convenient synthetic route to 2‐substituted benzotriazoles.
A new approach to the synthesis of 2 H‐benzotriazoles is described. This strategy is based on the copper‐catalyzed CN coupling of 2‐haloaryltriazenes or 2‐haloazo compounds with sodium azide and the intramolecular addition of a nitrene species to NN bonds (see scheme; TMEDA=N,N,N′,N′‐tetramethylethylenediamine; CTAB=hexadecyltrimethylammonium bromide). This approach allows the synthesis of various N‐amino‐ and N‐aryl‐2 H‐benzotriazoles in water, in good to excellent yields.</description><subject>benzotriazoles</subject><subject>cascade cyclizations</subject><subject>sodium azide</subject><subject>water</subject><issn>0947-6539</issn><issn>1521-3765</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2014</creationdate><recordtype>article</recordtype><recordid>eNqF0M9O3DAQBnCraqVuodee_QJebE8cx9xotMtSLSB1qfZoufFEa5pNVnFaSE5cK96SJ2H_IMSN08xhfp80HyHfBB8LzuVJscL1WHIBHLSQH8hIKCkY6FR9JCNuEs1SBeYz-RLjLefcpAAj8pg3mw22LHedq_oBPc1dLJxHmvdFFQbXhaamP9EV-6UpqWQzVzWu7auuDW7AGiN1taeLxoe_a3o2BI-ndIEVbsk_pIu-7lYYQ9zjp4f_M_Yd66HZ66ba6lDTpeuwPSafSldF_Poyj8iv6eQmn7H59flFfjZnBSRKMshUClJ4bnwBOvEKRKIyLBMhfGm89EpKz0sEn-rCqIwrkeoMQP82qRFlCUdkfMgt2ibGFku7acN6-5EV3O6qtLsq7WuVW2AO4C5U2L9zbfPZ5PKtZQcbYof3r9a1f2yqQSu7vDq3yx9zsZTTzObwDMKLiUg</recordid><startdate>20140210</startdate><enddate>20140210</enddate><creator>Shang, Xiaobo</creator><creator>Zhao, Shixian</creator><creator>Chen, Wanzhi</creator><creator>Chen, Chao</creator><creator>Qiu, Huayu</creator><general>WILEY-VCH Verlag</general><general>WILEY‐VCH Verlag</general><scope>BSCLL</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>20140210</creationdate><title>Copper-Catalyzed Cascade Cyclization Reaction of 2-Haloaryltriazenes and Sodium Azide: Selective Synthesis of 2 H-Benzotriazoles in Water</title><author>Shang, Xiaobo ; Zhao, Shixian ; Chen, Wanzhi ; Chen, Chao ; Qiu, Huayu</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3452-3856321d09dc374d531458ef411df9d2d522d0fe3d67c958051678337b9691ff3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2014</creationdate><topic>benzotriazoles</topic><topic>cascade cyclizations</topic><topic>sodium azide</topic><topic>water</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Shang, Xiaobo</creatorcontrib><creatorcontrib>Zhao, Shixian</creatorcontrib><creatorcontrib>Chen, Wanzhi</creatorcontrib><creatorcontrib>Chen, Chao</creatorcontrib><creatorcontrib>Qiu, Huayu</creatorcontrib><collection>Istex</collection><collection>CrossRef</collection><jtitle>Chemistry : a European journal</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Shang, Xiaobo</au><au>Zhao, Shixian</au><au>Chen, Wanzhi</au><au>Chen, Chao</au><au>Qiu, Huayu</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Copper-Catalyzed Cascade Cyclization Reaction of 2-Haloaryltriazenes and Sodium Azide: Selective Synthesis of 2 H-Benzotriazoles in Water</atitle><jtitle>Chemistry : a European journal</jtitle><addtitle>Chem. Eur. J</addtitle><date>2014-02-10</date><risdate>2014</risdate><volume>20</volume><issue>7</issue><spage>1825</spage><epage>1828</epage><pages>1825-1828</pages><issn>0947-6539</issn><eissn>1521-3765</eissn><abstract>A new approach to the synthesis of 2 H‐benzotriazoles is described. This strategy is based on the copper‐catalyzed CN coupling of 2‐haloaryltriazenes or 2‐haloazo compounds with sodium azide and the intramolecular addition of nitrene to NN bonds. This approach allows the synthesis of various N‐amino‐ and N‐aryl‐2 H‐benzotriazoles in water, in good to excellent yields. The procedure is simple and the starting materials and catalyst are easily available, offering a practical and convenient synthetic route to 2‐substituted benzotriazoles.
A new approach to the synthesis of 2 H‐benzotriazoles is described. This strategy is based on the copper‐catalyzed CN coupling of 2‐haloaryltriazenes or 2‐haloazo compounds with sodium azide and the intramolecular addition of a nitrene species to NN bonds (see scheme; TMEDA=N,N,N′,N′‐tetramethylethylenediamine; CTAB=hexadecyltrimethylammonium bromide). This approach allows the synthesis of various N‐amino‐ and N‐aryl‐2 H‐benzotriazoles in water, in good to excellent yields.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag</pub><doi>10.1002/chem.201303712</doi><tpages>4</tpages></addata></record> |
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| language | eng |
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| source | Wiley Online Library Journals Frontfile Complete |
| subjects | benzotriazoles cascade cyclizations sodium azide water |
| title | Copper-Catalyzed Cascade Cyclization Reaction of 2-Haloaryltriazenes and Sodium Azide: Selective Synthesis of 2 H-Benzotriazoles in Water |
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