Synthesis of Substituted 1H-Indazoles from Arynes and Hydrazones
The 1H-indazole skeleton can be constructed by a [3 + 2] annulation approach from arynes and hydrazones. Under different reaction conditions, both N-tosylhydrazones and N-aryl/alkylhydrazones can be used to afford a variety of indazoles. The former reaction affords 3-substituted indazoles either via...
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| Veröffentlicht in: | Journal of organic chemistry 2012-04, Vol.77 (7), p.3149-3158 |
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| container_end_page | 3158 |
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| container_issue | 7 |
| container_start_page | 3149 |
| container_title | Journal of organic chemistry |
| container_volume | 77 |
| creator | Li, Pan Wu, Chunrui Zhao, Jingjing Rogness, Donald C Shi, Feng |
| description | The 1H-indazole skeleton can be constructed by a [3 + 2] annulation approach from arynes and hydrazones. Under different reaction conditions, both N-tosylhydrazones and N-aryl/alkylhydrazones can be used to afford a variety of indazoles. The former reaction affords 3-substituted indazoles either via in situ generated diazo compounds or through an annulation/elimination process. The latter reaction leads to 1,3-disubstituted indazoles likely through an annulation/oxidation process. The reactions operate under mild conditions and can accommodate aryl, vinyl, and less satisfactorily, alkyl groups. |
| doi_str_mv | 10.1021/jo202598e |
| format | Article |
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Under different reaction conditions, both N-tosylhydrazones and N-aryl/alkylhydrazones can be used to afford a variety of indazoles. The former reaction affords 3-substituted indazoles either via in situ generated diazo compounds or through an annulation/elimination process. The latter reaction leads to 1,3-disubstituted indazoles likely through an annulation/oxidation process. The reactions operate under mild conditions and can accommodate aryl, vinyl, and less satisfactorily, alkyl groups.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/jo202598e</identifier><identifier>PMID: 22414117</identifier><identifier>CODEN: JOCEAH</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Catalysis ; Chemistry ; Exact sciences and technology ; Heterocyclic compounds ; Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings ; Hydrazones - chemistry ; Indazoles - chemical synthesis ; Indazoles - chemistry ; Molecular Structure ; Organic chemistry ; Oxidation-Reduction ; Preparations and properties ; Stereoisomerism</subject><ispartof>Journal of organic chemistry, 2012-04, Vol.77 (7), p.3149-3158</ispartof><rights>Copyright © 2012 American Chemical Society</rights><rights>2015 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/jo202598e$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jo202598e$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,776,780,27053,27901,27902,56713,56763</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=25778563$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/22414117$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Li, Pan</creatorcontrib><creatorcontrib>Wu, Chunrui</creatorcontrib><creatorcontrib>Zhao, Jingjing</creatorcontrib><creatorcontrib>Rogness, Donald C</creatorcontrib><creatorcontrib>Shi, Feng</creatorcontrib><title>Synthesis of Substituted 1H-Indazoles from Arynes and Hydrazones</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>The 1H-indazole skeleton can be constructed by a [3 + 2] annulation approach from arynes and hydrazones. Under different reaction conditions, both N-tosylhydrazones and N-aryl/alkylhydrazones can be used to afford a variety of indazoles. The former reaction affords 3-substituted indazoles either via in situ generated diazo compounds or through an annulation/elimination process. The latter reaction leads to 1,3-disubstituted indazoles likely through an annulation/oxidation process. The reactions operate under mild conditions and can accommodate aryl, vinyl, and less satisfactorily, alkyl groups.</description><subject>Catalysis</subject><subject>Chemistry</subject><subject>Exact sciences and technology</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings</subject><subject>Hydrazones - chemistry</subject><subject>Indazoles - chemical synthesis</subject><subject>Indazoles - chemistry</subject><subject>Molecular Structure</subject><subject>Organic chemistry</subject><subject>Oxidation-Reduction</subject><subject>Preparations and properties</subject><subject>Stereoisomerism</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2012</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNpFkDFPwzAQhS0EoqUw8AdQFsQUsM-1Y2-gCmilSgyF2brEjkiVxMVOhvDrSUWht9yd7tPpvUfINaP3jAJ72HqgILRyJ2TKBNBUajo_JVNKAVIOkk_IRYxbOpYQ4pxMAOZszlg2JY-boe0-Xaxi4stk0-exq7q-czZhy3TVWvz2tYtJGXyTPIWhHWdsbbIcbBhP43pJzkqso7s69Bn5eHl-XyzT9dvravG0ThGk7FLQijEseObA5VQybVFzpxDAOlRSUMtzxbXUPCtHZRq0U4yj1EBVgVrwGbn7_bsL_qt3sTNNFQtX19g630ejNSjQjO_JmwPZ542zZheqBsNg_kyPwO0BwFhgXQZsiyoeOZFlSkh-5LCIZuv70I4GDaNmH7r5D53_ABhbbuk</recordid><startdate>20120406</startdate><enddate>20120406</enddate><creator>Li, Pan</creator><creator>Wu, Chunrui</creator><creator>Zhao, Jingjing</creator><creator>Rogness, Donald C</creator><creator>Shi, Feng</creator><general>American Chemical Society</general><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>7X8</scope></search><sort><creationdate>20120406</creationdate><title>Synthesis of Substituted 1H-Indazoles from Arynes and Hydrazones</title><author>Li, Pan ; Wu, Chunrui ; Zhao, Jingjing ; Rogness, Donald C ; Shi, Feng</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a266t-29811ac37e2eb0619da93e8a22dea8650d3b8396937f411929e813a69208ca953</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2012</creationdate><topic>Catalysis</topic><topic>Chemistry</topic><topic>Exact sciences and technology</topic><topic>Heterocyclic compounds</topic><topic>Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings</topic><topic>Hydrazones - chemistry</topic><topic>Indazoles - chemical synthesis</topic><topic>Indazoles - chemistry</topic><topic>Molecular Structure</topic><topic>Organic chemistry</topic><topic>Oxidation-Reduction</topic><topic>Preparations and properties</topic><topic>Stereoisomerism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Li, Pan</creatorcontrib><creatorcontrib>Wu, Chunrui</creatorcontrib><creatorcontrib>Zhao, Jingjing</creatorcontrib><creatorcontrib>Rogness, Donald C</creatorcontrib><creatorcontrib>Shi, Feng</creatorcontrib><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Li, Pan</au><au>Wu, Chunrui</au><au>Zhao, Jingjing</au><au>Rogness, Donald C</au><au>Shi, Feng</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis of Substituted 1H-Indazoles from Arynes and Hydrazones</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. Org. Chem</addtitle><date>2012-04-06</date><risdate>2012</risdate><volume>77</volume><issue>7</issue><spage>3149</spage><epage>3158</epage><pages>3149-3158</pages><issn>0022-3263</issn><eissn>1520-6904</eissn><coden>JOCEAH</coden><abstract>The 1H-indazole skeleton can be constructed by a [3 + 2] annulation approach from arynes and hydrazones. Under different reaction conditions, both N-tosylhydrazones and N-aryl/alkylhydrazones can be used to afford a variety of indazoles. The former reaction affords 3-substituted indazoles either via in situ generated diazo compounds or through an annulation/elimination process. The latter reaction leads to 1,3-disubstituted indazoles likely through an annulation/oxidation process. The reactions operate under mild conditions and can accommodate aryl, vinyl, and less satisfactorily, alkyl groups.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>22414117</pmid><doi>10.1021/jo202598e</doi><tpages>10</tpages></addata></record> |
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| subjects | Catalysis Chemistry Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings Hydrazones - chemistry Indazoles - chemical synthesis Indazoles - chemistry Molecular Structure Organic chemistry Oxidation-Reduction Preparations and properties Stereoisomerism |
| title | Synthesis of Substituted 1H-Indazoles from Arynes and Hydrazones |
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