Improved Regioselectivity in Pyrazole Formation through the Use of Fluorinated Alcohols as Solvents: Synthesis and Biological Activity of Fluorinated Tebufenpyrad Analogs

The preparation of N-methylpyrazoles is usually accomplished through reaction of a suitable 1,3-diketone with methylhydrazine in ethanol as the solvent. This strategy, however, leads to the formation of regioisomeric mixtures of N-methylpyrazoles, which sometimes are difficult to separate. We have d...

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Veröffentlicht in:	Journal of organic chemistry 2008-05, Vol.73 (9), p.3523-3529
Hauptverfasser:	Fustero, Santos, Román, Raquel, Sanz-Cervera, Juan F, Simón-Fuentes, Antonio, Cuñat, Ana C, Villanova, Salvador, Murguía, Marcelo
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Sprache:	eng
Schlagworte:	Acari - drug effects Alcohols - chemistry Animals Chemistry Exact sciences and technology Fluorine Compounds - chemical synthesis Fluorine Compounds - chemistry Fluorine Compounds - pharmacology Heterocyclic compounds Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings Methylation Molecular Structure Organic chemistry Phenylhydrazines - chemistry Preparations and properties Pyrazoles - chemical synthesis Pyrazoles - chemistry Pyrazoles - pharmacology Solvents - chemistry Stereoisomerism
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container_title	Journal of organic chemistry
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creator	Fustero, Santos Román, Raquel Sanz-Cervera, Juan F Simón-Fuentes, Antonio Cuñat, Ana C Villanova, Salvador Murguía, Marcelo
description	The preparation of N-methylpyrazoles is usually accomplished through reaction of a suitable 1,3-diketone with methylhydrazine in ethanol as the solvent. This strategy, however, leads to the formation of regioisomeric mixtures of N-methylpyrazoles, which sometimes are difficult to separate. We have determined that the use of fluorinated alcohols such as 2,2,2-trifluoroethanol (TFE) and 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP) as solvents dramatically increases the regioselectivity in the pyrazole formation, and we have used this modification in a straightforward synthesis of fluorinated analogs of Tebufenpyrad with acaricide activity.
doi_str_mv	10.1021/jo800251g
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This strategy, however, leads to the formation of regioisomeric mixtures of N-methylpyrazoles, which sometimes are difficult to separate. We have determined that the use of fluorinated alcohols such as 2,2,2-trifluoroethanol (TFE) and 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP) as solvents dramatically increases the regioselectivity in the pyrazole formation, and we have used this modification in a straightforward synthesis of fluorinated analogs of Tebufenpyrad with acaricide activity.</description><identifier>ISSN: 0022-3263</identifier><identifier>EISSN: 1520-6904</identifier><identifier>DOI: 10.1021/jo800251g</identifier><identifier>PMID: 18399658</identifier><identifier>CODEN: JOCEAH</identifier><language>eng</language><publisher>Washington, DC: American Chemical Society</publisher><subject>Acari - drug effects ; Alcohols - chemistry ; Animals ; Chemistry ; Exact sciences and technology ; Fluorine Compounds - chemical synthesis ; Fluorine Compounds - chemistry ; Fluorine Compounds - pharmacology ; Heterocyclic compounds ; Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings ; Methylation ; Molecular Structure ; Organic chemistry ; Phenylhydrazines - chemistry ; Preparations and properties ; Pyrazoles - chemical synthesis ; Pyrazoles - chemistry ; Pyrazoles - pharmacology ; Solvents - chemistry ; Stereoisomerism</subject><ispartof>Journal of organic chemistry, 2008-05, Vol.73 (9), p.3523-3529</ispartof><rights>Copyright © 2008 American Chemical Society</rights><rights>2008 INIST-CNRS</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a482t-726956c35522ef2c1000b961dfabcdf6bdc3c1b1500980a5e32f3edcb3ef62ed3</citedby><cites>FETCH-LOGICAL-a482t-726956c35522ef2c1000b961dfabcdf6bdc3c1b1500980a5e32f3edcb3ef62ed3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/jo800251g$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/jo800251g$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>315,781,785,2766,27078,27926,27927,56740,56790</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=20301175$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/18399658$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Fustero, Santos</creatorcontrib><creatorcontrib>Román, Raquel</creatorcontrib><creatorcontrib>Sanz-Cervera, Juan F</creatorcontrib><creatorcontrib>Simón-Fuentes, Antonio</creatorcontrib><creatorcontrib>Cuñat, Ana C</creatorcontrib><creatorcontrib>Villanova, Salvador</creatorcontrib><creatorcontrib>Murguía, Marcelo</creatorcontrib><title>Improved Regioselectivity in Pyrazole Formation through the Use of Fluorinated Alcohols as Solvents: Synthesis and Biological Activity of Fluorinated Tebufenpyrad Analogs</title><title>Journal of organic chemistry</title><addtitle>J. Org. Chem</addtitle><description>The preparation of N-methylpyrazoles is usually accomplished through reaction of a suitable 1,3-diketone with methylhydrazine in ethanol as the solvent. This strategy, however, leads to the formation of regioisomeric mixtures of N-methylpyrazoles, which sometimes are difficult to separate. We have determined that the use of fluorinated alcohols such as 2,2,2-trifluoroethanol (TFE) and 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP) as solvents dramatically increases the regioselectivity in the pyrazole formation, and we have used this modification in a straightforward synthesis of fluorinated analogs of Tebufenpyrad with acaricide activity.</description><subject>Acari - drug effects</subject><subject>Alcohols - chemistry</subject><subject>Animals</subject><subject>Chemistry</subject><subject>Exact sciences and technology</subject><subject>Fluorine Compounds - chemical synthesis</subject><subject>Fluorine Compounds - chemistry</subject><subject>Fluorine Compounds - pharmacology</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>Methylation</subject><subject>Molecular Structure</subject><subject>Organic chemistry</subject><subject>Phenylhydrazines - chemistry</subject><subject>Preparations and properties</subject><subject>Pyrazoles - chemical synthesis</subject><subject>Pyrazoles - chemistry</subject><subject>Pyrazoles - pharmacology</subject><subject>Solvents - chemistry</subject><subject>Stereoisomerism</subject><issn>0022-3263</issn><issn>1520-6904</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2008</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNptkd-KEzEUxoMobl298AUkNwpejObPJJ3xrq52XViw2C6INyGTOWmzZibdZKZYH8mnNNLaBTE3B05-fOec70PoOSVvKGH07W2oCGGCrh-gCRWMFLIm5UM0yU1WcCb5GXqS0i3JTwjxGJ3Rite1FNUE_brqtjHsoMVfYO1CAg9mcDs37LHr8WIf9c_gAc9D7PTgQo-HTQzjepMr4JsEOFg892OIrtdDVpl5EzbBJ6wTXga_g35I7_By32c-udzuW_zeBR_WzmiPZ3-H_SOzgma00G_z_KzZ68ynp-iR1T7Bs2M9Rzfzj6uLT8X158uri9l1ocuKDcWUyVpIw4VgDCwzNF_d1JK2VjemtbJpDTe0oYKQuiJaAGeWQ2saDlYyaPk5enXQzcbcjZAG1blkwHvdQxiTkjUtecnqDL4-gCaGlCJYtY2u03GvKFF_glGnYDL74ig6Nh209-QxiQy8PAI6ZWds1L1x6cQxwgmlU5G54sC5NMCP07-O35Wc8qlQq8VSMf7h6-JbydXlva42Ke8zxmxm-s-CvwGU_7Us</recordid><startdate>20080502</startdate><enddate>20080502</enddate><creator>Fustero, Santos</creator><creator>Román, Raquel</creator><creator>Sanz-Cervera, Juan F</creator><creator>Simón-Fuentes, Antonio</creator><creator>Cuñat, Ana C</creator><creator>Villanova, Salvador</creator><creator>Murguía, Marcelo</creator><general>American Chemical Society</general><scope>BSCLL</scope><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20080502</creationdate><title>Improved Regioselectivity in Pyrazole Formation through the Use of Fluorinated Alcohols as Solvents: Synthesis and Biological Activity of Fluorinated Tebufenpyrad Analogs</title><author>Fustero, Santos ; Román, Raquel ; Sanz-Cervera, Juan F ; Simón-Fuentes, Antonio ; Cuñat, Ana C ; Villanova, Salvador ; Murguía, Marcelo</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-a482t-726956c35522ef2c1000b961dfabcdf6bdc3c1b1500980a5e32f3edcb3ef62ed3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2008</creationdate><topic>Acari - drug effects</topic><topic>Alcohols - chemistry</topic><topic>Animals</topic><topic>Chemistry</topic><topic>Exact sciences and technology</topic><topic>Fluorine Compounds - chemical synthesis</topic><topic>Fluorine Compounds - chemistry</topic><topic>Fluorine Compounds - pharmacology</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>Methylation</topic><topic>Molecular Structure</topic><topic>Organic chemistry</topic><topic>Phenylhydrazines - chemistry</topic><topic>Preparations and properties</topic><topic>Pyrazoles - chemical synthesis</topic><topic>Pyrazoles - chemistry</topic><topic>Pyrazoles - pharmacology</topic><topic>Solvents - chemistry</topic><topic>Stereoisomerism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Fustero, Santos</creatorcontrib><creatorcontrib>Román, Raquel</creatorcontrib><creatorcontrib>Sanz-Cervera, Juan F</creatorcontrib><creatorcontrib>Simón-Fuentes, Antonio</creatorcontrib><creatorcontrib>Cuñat, Ana C</creatorcontrib><creatorcontrib>Villanova, Salvador</creatorcontrib><creatorcontrib>Murguía, Marcelo</creatorcontrib><collection>Istex</collection><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Journal of organic chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Fustero, Santos</au><au>Román, Raquel</au><au>Sanz-Cervera, Juan F</au><au>Simón-Fuentes, Antonio</au><au>Cuñat, Ana C</au><au>Villanova, Salvador</au><au>Murguía, Marcelo</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Improved Regioselectivity in Pyrazole Formation through the Use of Fluorinated Alcohols as Solvents: Synthesis and Biological Activity of Fluorinated Tebufenpyrad Analogs</atitle><jtitle>Journal of organic chemistry</jtitle><addtitle>J. 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We have determined that the use of fluorinated alcohols such as 2,2,2-trifluoroethanol (TFE) and 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP) as solvents dramatically increases the regioselectivity in the pyrazole formation, and we have used this modification in a straightforward synthesis of fluorinated analogs of Tebufenpyrad with acaricide activity.</abstract><cop>Washington, DC</cop><pub>American Chemical Society</pub><pmid>18399658</pmid><doi>10.1021/jo800251g</doi><tpages>7</tpages><oa>free_for_read</oa></addata></record>
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subjects	Acari - drug effects Alcohols - chemistry Animals Chemistry Exact sciences and technology Fluorine Compounds - chemical synthesis Fluorine Compounds - chemistry Fluorine Compounds - pharmacology Heterocyclic compounds Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings Methylation Molecular Structure Organic chemistry Phenylhydrazines - chemistry Preparations and properties Pyrazoles - chemical synthesis Pyrazoles - chemistry Pyrazoles - pharmacology Solvents - chemistry Stereoisomerism
title	Improved Regioselectivity in Pyrazole Formation through the Use of Fluorinated Alcohols as Solvents: Synthesis and Biological Activity of Fluorinated Tebufenpyrad Analogs
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