A Practical, Metal-Free Synthesis of 1H-Indazoles

The synthesis of 1H-indazoles is achieved from o-aminobenzoximes by the selective activation of the oxime in the presence of the amino group. The reaction occurs with a variety of substituted o-aminobenzoximes using a slight excess of methanesulfonyl chloride and triethylamine at 0−23 °C and is amen...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Organic letters 2008-03, Vol.10 (5), p.1021-1023
Hauptverfasser: Counceller, Carla M, Eichman, Chad C, Wray, Brenda C, Stambuli, James P
Format: Artikel
Sprache:eng
Schlagworte:
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 1023
container_issue 5
container_start_page 1021
container_title Organic letters
container_volume 10
creator Counceller, Carla M
Eichman, Chad C
Wray, Brenda C
Stambuli, James P
description The synthesis of 1H-indazoles is achieved from o-aminobenzoximes by the selective activation of the oxime in the presence of the amino group. The reaction occurs with a variety of substituted o-aminobenzoximes using a slight excess of methanesulfonyl chloride and triethylamine at 0−23 °C and is amenable to scale-up. The synthesis of 1H-indazoles under these conditions is extremely mild compared with previous synthetic approaches and affords the desired compounds in good to excellent yields.
doi_str_mv 10.1021/ol800053f
format Article
fullrecord <record><control><sourceid>proquest_pubme</sourceid><recordid>TN_cdi_proquest_miscellaneous_70347730</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>70347730</sourcerecordid><originalsourceid>FETCH-LOGICAL-a169t-29b1911375f7affb9d5f95e0a5990201d9353a0d8ccef565073667d55b45da4c3</originalsourceid><addsrcrecordid>eNo9kM1OwzAQhC0EoqVw4AVQLnAisGvHcX2sKkorFYEEnC3HPyKVk5Q4OZSnJ6ilpxmNPo12h5BrhAcEio9NmAIAZ_6EjJFTlgrg9PTocxiRixg3ADgk8pyMcEqplCwfE5wlb602XWl0uE9eXKdDumidS953dfflYhmTxie4TFe11T9NcPGSnHkdors66IR8Lp4-5st0_fq8ms_WqcZcdimVBUpEJrgX2vtCWu4ld6C5lEABrWScabBTY5znOQfB8lxYzouMW50ZNiF3-95t23z3LnaqKqNxIejaNX1UAlgmBIMBvDmAfVE5q7ZtWel2p_6fHIDbPaBNVJumb-vhboWg_sZTx_HYL6SEW8Y</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>70347730</pqid></control><display><type>article</type><title>A Practical, Metal-Free Synthesis of 1H-Indazoles</title><source>MEDLINE</source><source>American Chemical Society Journals</source><creator>Counceller, Carla M ; Eichman, Chad C ; Wray, Brenda C ; Stambuli, James P</creator><creatorcontrib>Counceller, Carla M ; Eichman, Chad C ; Wray, Brenda C ; Stambuli, James P</creatorcontrib><description>The synthesis of 1H-indazoles is achieved from o-aminobenzoximes by the selective activation of the oxime in the presence of the amino group. The reaction occurs with a variety of substituted o-aminobenzoximes using a slight excess of methanesulfonyl chloride and triethylamine at 0−23 °C and is amenable to scale-up. The synthesis of 1H-indazoles under these conditions is extremely mild compared with previous synthetic approaches and affords the desired compounds in good to excellent yields.</description><identifier>ISSN: 1523-7060</identifier><identifier>EISSN: 1523-7052</identifier><identifier>DOI: 10.1021/ol800053f</identifier><identifier>PMID: 18229936</identifier><language>eng</language><publisher>United States: American Chemical Society</publisher><subject>Catalysis ; Combinatorial Chemistry Techniques ; Indazoles - chemical synthesis ; Indazoles - chemistry ; Molecular Structure ; Oximes - chemistry</subject><ispartof>Organic letters, 2008-03, Vol.10 (5), p.1021-1023</ispartof><rights>Copyright © 2008 American Chemical Society</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/ol800053f$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/ol800053f$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,780,784,27076,27924,27925,56738,56788</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/18229936$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Counceller, Carla M</creatorcontrib><creatorcontrib>Eichman, Chad C</creatorcontrib><creatorcontrib>Wray, Brenda C</creatorcontrib><creatorcontrib>Stambuli, James P</creatorcontrib><title>A Practical, Metal-Free Synthesis of 1H-Indazoles</title><title>Organic letters</title><addtitle>Org. Lett</addtitle><description>The synthesis of 1H-indazoles is achieved from o-aminobenzoximes by the selective activation of the oxime in the presence of the amino group. The reaction occurs with a variety of substituted o-aminobenzoximes using a slight excess of methanesulfonyl chloride and triethylamine at 0−23 °C and is amenable to scale-up. The synthesis of 1H-indazoles under these conditions is extremely mild compared with previous synthetic approaches and affords the desired compounds in good to excellent yields.</description><subject>Catalysis</subject><subject>Combinatorial Chemistry Techniques</subject><subject>Indazoles - chemical synthesis</subject><subject>Indazoles - chemistry</subject><subject>Molecular Structure</subject><subject>Oximes - chemistry</subject><issn>1523-7060</issn><issn>1523-7052</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2008</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNo9kM1OwzAQhC0EoqVw4AVQLnAisGvHcX2sKkorFYEEnC3HPyKVk5Q4OZSnJ6ilpxmNPo12h5BrhAcEio9NmAIAZ_6EjJFTlgrg9PTocxiRixg3ADgk8pyMcEqplCwfE5wlb602XWl0uE9eXKdDumidS953dfflYhmTxie4TFe11T9NcPGSnHkdors66IR8Lp4-5st0_fq8ms_WqcZcdimVBUpEJrgX2vtCWu4ld6C5lEABrWScabBTY5znOQfB8lxYzouMW50ZNiF3-95t23z3LnaqKqNxIejaNX1UAlgmBIMBvDmAfVE5q7ZtWel2p_6fHIDbPaBNVJumb-vhboWg_sZTx_HYL6SEW8Y</recordid><startdate>20080306</startdate><enddate>20080306</enddate><creator>Counceller, Carla M</creator><creator>Eichman, Chad C</creator><creator>Wray, Brenda C</creator><creator>Stambuli, James P</creator><general>American Chemical Society</general><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>7X8</scope></search><sort><creationdate>20080306</creationdate><title>A Practical, Metal-Free Synthesis of 1H-Indazoles</title><author>Counceller, Carla M ; Eichman, Chad C ; Wray, Brenda C ; Stambuli, James P</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a169t-29b1911375f7affb9d5f95e0a5990201d9353a0d8ccef565073667d55b45da4c3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2008</creationdate><topic>Catalysis</topic><topic>Combinatorial Chemistry Techniques</topic><topic>Indazoles - chemical synthesis</topic><topic>Indazoles - chemistry</topic><topic>Molecular Structure</topic><topic>Oximes - chemistry</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Counceller, Carla M</creatorcontrib><creatorcontrib>Eichman, Chad C</creatorcontrib><creatorcontrib>Wray, Brenda C</creatorcontrib><creatorcontrib>Stambuli, James P</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>MEDLINE - Academic</collection><jtitle>Organic letters</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Counceller, Carla M</au><au>Eichman, Chad C</au><au>Wray, Brenda C</au><au>Stambuli, James P</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>A Practical, Metal-Free Synthesis of 1H-Indazoles</atitle><jtitle>Organic letters</jtitle><addtitle>Org. Lett</addtitle><date>2008-03-06</date><risdate>2008</risdate><volume>10</volume><issue>5</issue><spage>1021</spage><epage>1023</epage><pages>1021-1023</pages><issn>1523-7060</issn><eissn>1523-7052</eissn><abstract>The synthesis of 1H-indazoles is achieved from o-aminobenzoximes by the selective activation of the oxime in the presence of the amino group. The reaction occurs with a variety of substituted o-aminobenzoximes using a slight excess of methanesulfonyl chloride and triethylamine at 0−23 °C and is amenable to scale-up. The synthesis of 1H-indazoles under these conditions is extremely mild compared with previous synthetic approaches and affords the desired compounds in good to excellent yields.</abstract><cop>United States</cop><pub>American Chemical Society</pub><pmid>18229936</pmid><doi>10.1021/ol800053f</doi><tpages>3</tpages></addata></record>
fulltext fulltext
identifier ISSN: 1523-7060
ispartof Organic letters, 2008-03, Vol.10 (5), p.1021-1023
issn 1523-7060
1523-7052
language eng
recordid cdi_proquest_miscellaneous_70347730
source MEDLINE; American Chemical Society Journals
subjects Catalysis
Combinatorial Chemistry Techniques
Indazoles - chemical synthesis
Indazoles - chemistry
Molecular Structure
Oximes - chemistry
title A Practical, Metal-Free Synthesis of 1H-Indazoles
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-23T19%3A25%3A47IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_pubme&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=A%20Practical,%20Metal-Free%20Synthesis%20of%201H-Indazoles&rft.jtitle=Organic%20letters&rft.au=Counceller,%20Carla%20M&rft.date=2008-03-06&rft.volume=10&rft.issue=5&rft.spage=1021&rft.epage=1023&rft.pages=1021-1023&rft.issn=1523-7060&rft.eissn=1523-7052&rft_id=info:doi/10.1021/ol800053f&rft_dat=%3Cproquest_pubme%3E70347730%3C/proquest_pubme%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=70347730&rft_id=info:pmid/18229936&rfr_iscdi=true