Alternative approaches to the synthesis of polyfluoroalkyl-containing 1-methyl-4-nitrosopyrazoles
We studied different approaches to the synthesis of polyfluoroalkyl-containing 1-methyl-4-nitrosopyrazoles, which are based on the cyclization of 4,4,4-trifluoro-3,3-dihydroxy-2-hydroxyimino-1-R-butan-1-ones or 2-hydroxyimino-1,3-diketones with methylhydrazine and on a one-pot sequential treatment o...
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| Published in | Russian chemical bulletin Vol. 70; no. 6; pp. 1135 - 1140 |
|---|---|
| Main Authors | , , , , |
| Format | Journal Article |
| Language | English |
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New York
Springer US
01.06.2021
Springer Nature B.V |
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| Abstract | We studied different approaches to the synthesis of polyfluoroalkyl-containing 1-methyl-4-nitrosopyrazoles, which are based on the cyclization of 4,4,4-trifluoro-3,3-dihydroxy-2-hydroxyimino-1-R-butan-1-ones or 2-hydroxyimino-1,3-diketones with methylhydrazine and on a one-pot sequential treatment of 1,3-diketones with sodium nitrite and methylhydrazine. It was found that the regioselectivity of the formation of 1-methyl-4-nitrosopyrazoles is affected by the steric factors of 1,3-dicarbonyl reagents. The study of the mycostatic effect of 4-nitrosopyrazoles showed that the introduction of a bulky polyfluoroalkyl or
tert
-butyl substituent leads to a decrease in their activity. |
|---|---|
| AbstractList | We studied different approaches to the synthesis of polyfluoroalkyl-containing 1-methyl-4-nitrosopyrazoles, which are based on the cyclization of 4,4,4-trifluoro-3,3-dihydroxy-2-hydroxyimino-1-R-butan-1-ones or 2-hydroxyimino-1,3-diketones with methylhydrazine and on a one-pot sequential treatment of 1,3-diketones with sodium nitrite and methylhydrazine. It was found that the regioselectivity of the formation of 1-methyl-4-nitrosopyrazoles is affected by the steric factors of 1,3-dicarbonyl reagents. The study of the mycostatic effect of 4-nitrosopyrazoles showed that the introduction of a bulky polyfluoroalkyl or tert-butyl substituent leads to a decrease in their activity. We studied different approaches to the synthesis of polyfluoroalkyl-containing 1-methyl-4-nitrosopyrazoles, which are based on the cyclization of 4,4,4-trifluoro-3,3-dihydroxy-2-hydroxyimino-1-R-butan-1-ones or 2-hydroxyimino-1,3-diketones with methylhydrazine and on a one-pot sequential treatment of 1,3-diketones with sodium nitrite and methylhydrazine. It was found that the regioselectivity of the formation of 1-methyl-4-nitrosopyrazoles is affected by the steric factors of 1,3-dicarbonyl reagents. The study of the mycostatic effect of 4-nitrosopyrazoles showed that the introduction of a bulky polyfluoroalkyl or tert -butyl substituent leads to a decrease in their activity. |
| Author | Gerasimova, N. A. Agafonova, N. A. Saloutin, V. I. Evstigneeva, N. P. Burgart, Ya. V. |
| Author_xml | – sequence: 1 givenname: N. A. surname: Agafonova fullname: Agafonova, N. A. organization: I. Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences – sequence: 2 givenname: Ya. V. surname: Burgart fullname: Burgart, Ya. V. organization: I. Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences – sequence: 3 givenname: N. A. surname: Gerasimova fullname: Gerasimova, N. A. organization: Ural Research Institute of Dermatovenerology and Immunopathology – sequence: 4 givenname: N. P. surname: Evstigneeva fullname: Evstigneeva, N. P. organization: Ural Research Institute of Dermatovenerology and Immunopathology – sequence: 5 givenname: V. I. surname: Saloutin fullname: Saloutin, V. I. email: saloutin@ios.uran.ru organization: I. Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences |
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| Keywords | mycostatic activity 1-methyl-4-nitrosopyrazoles 4,4,4-trifluoro-3,3-dihydroxy-2-(hydroxyimino)butan-1-ones polyfluoroalkyl-2-hydroxyimino-1,3-diketones |
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| References | ZafraniYYeffetDSod-MoriahGBerlinerAAmirDMarcianoDGershonovESaphierSJ. Med. Chem.2017607971:CAS:528:DC%2BC2sXis12jtw%3D%3D10.1021/acs.jmedchem.6b01691 BurgartY VAgafonovaN AShchegolkovE VKrasnykhO PKushchS OEvstigneevaN PGerasimovaN AMaslovaV VTriandafilovaG ASolodnikovS YUlitkoM VMakhaevaG FRudakovaE VBorisevichS SZilberbergN VKungurovN VSaloutinV IChupakhinO NEur. J. Med. Chem.20202081127681:CAS:528:DC%2BB3cXhvVWgtbzO10.1016/j.ejmech.2020.112768 SheldrickG MActa Crystallogr., Sect. A: Found. Crystallogr.2008641121:CAS:528:DC%2BD2sXhsVGhurzO10.1107/S0108767307043930 HavrylyukDRomanOLesykREur. J. Med. Chem.20161131451:CAS:528:DC%2BC28Xjt1yqtb8%3D10.1016/j.ejmech.2016.02.030 PolitanskayaL VSelivanovaG APanteleevaE VTretyakovE VPlatonovV ENikul’shinP VVinogradovA SZonovY VKarpovV MMezhenkovaT VVasilyevA VKoldobskiiA BShilovaO SMorozovaS MBurgartY VShchegolkovE VSaloutinV ISokolovV BAksinenkoA YNenajdenkoV GMoskalikM YAstakhovaV VShainyanB ATabolinA AIoffeS LMuzalevskiyV MBalenkovaE SShastinA VTyutyunovA ABoikoV EIgumnovS MDilmanA DAdoninN YBardinV VMasoudS MVorobyevaD VOsipovS NNosovaE VLipunovaG NCharushinV NPrimaD OMakarovA GZibarevA VTrofimovB ASobeninaL NBelyaevaK VSosnovskikhV YObydennovD LUsachevS ARuss. Chem. Rev.2019884251:CAS:528:DC%2BC1MXhsFSqur3L10.1070/RCR4871 SaloutinV IBurgartY VSkryabinaZ EKuzuevaO GJ. Fluorine Chem.1997841071:CAS:528:DyaK2sXms1Kgs7k%3D10.1016/S0022-1139(97)00054-7 KüçükgüzelŞ G GŞenkardeşSEur. J. Med. Chem.20159778610.1016/j.ejmech.2014.11.059 R. Pérez-Fernández, P. Goya, J. Elguero, Arkivoc, 2014, Part ii, 233; DOI: https://doi.org/10.3998/ark.5550190.p008.131. Nitrofural, https://www.drugbank.ca/drugs/DB00336. BurgartY VAgafonovaN AShchegolkovE VMaslovaV VTriandafilovaG ASolodnikovS YKrasnykhO PSaloutinV IChem. Heterocycl. Compd.201955521:CAS:528:DC%2BC1MXnvFKjtr4%3D10.1007/s10593-019-02418-4 AnsariAAliAAsifMShamsuzzamanSNew J. Chem.201741161:CAS:528:DC%2BC28XhvVOjsLzI10.1039/C6NJ03181A MykhailiukP KChem. Rev.2021121310.1021/acs.chemrev.0c010151670 KaurKKumarVGuptaG KJ. Fluorine Chem.20151783061:CAS:528:DC%2BC2MXhsVensrvK10.1016/j.jfluchem.2015.08.015 O’HaganDJ. Fluorine Chem.2010131107110.1016/j.jfluchem.2010.03.003 KhudinaO GBurgartY VSaloutinV IKravchenkoM ARuss. J. Org. Chem.2011479041:CAS:528:DC%2BC3MXos1Sntr8%3D10.1134/S1070428011060121 BazhinD NKudyakovaY SNemytovaN ABurgartY VSaloutinV IJ. Fluorine Chem.2016186281:CAS:528:DC%2BC28XmsFyqt7k%3D10.1016/j.jfluchem.2016.04.009 PizzutiLBarschakAStefanelloFFariasMLencinaCRoesch-ElyMCunicoWMouraSPereiraCCurr. Org. Chem.2014181151:CAS:528:DC%2BC2cXis1aitL8%3D10.2174/13852728113179990029 J. C. Sloop, C. Holder, M. Henary, Eur. J. Org. Chem., 2015, 3405; DOI: https://doi.org/10.1002/ejoc.201500258. KhudinaO GBurgartY VSaloutinV IKravchenkoM ARuss. Chem. Bull.20105919671:CAS:528:DC%2BC3MXjtVKktrg%3D10.1007/s11172-010-0341-7 Vega-TeijidoMCaracelliIZukerman-SchpectorJJ. Mol. Graph. Model.2006243491:CAS:528:DC%2BD28XitVKgtLg%3D10.1016/j.jmgm.2005.09.008 WangJSánchez-RosellóMAceñaJ Ldel PozoCSorochinskyA EFusteroSSoloshonokV ALiuHChem. Rev.201411424321:CAS:528:DC%2BC3sXhvFegsb7I10.1021/cr4002879 A Ansari (3195_CR5) 2017; 41 P K Mykhailiuk (3195_CR6) 2021; 121 Y V Burgart (3195_CR13) 2020; 208 M Vega-Teijido (3195_CR15) 2006; 24 3195_CR8 Y V Burgart (3195_CR20) 2019; 55 Y Zafrani (3195_CR11) 2017; 60 O G Khudina (3195_CR17) 2011; 47 G M Sheldrick (3195_CR21) 2008; 64 D Havrylyuk (3195_CR4) 2016; 113 3195_CR2 D O’Hagan (3195_CR9) 2010; 131 J Wang (3195_CR10) 2014; 114 Ş G G Küçükgüzel (3195_CR3) 2015; 97 O G Khudina (3195_CR18) 2010; 59 D N Bazhin (3195_CR19) 2016; 186 L Pizzuti (3195_CR1) 2014; 18 K Kaur (3195_CR7) 2015; 178 3195_CR14 V I Saloutin (3195_CR16) 1997; 84 L V Politanskaya (3195_CR12) 2019; 88 |
| References_xml | – volume: 18 start-page: 115 year: 2014 ident: 3195_CR1 publication-title: Curr. Org. Chem. doi: 10.2174/13852728113179990029 contributor: fullname: L Pizzuti – volume: 208 start-page: 112768 year: 2020 ident: 3195_CR13 publication-title: Eur. J. Med. Chem. doi: 10.1016/j.ejmech.2020.112768 contributor: fullname: Y V Burgart – ident: 3195_CR14 – volume: 41 start-page: 16 year: 2017 ident: 3195_CR5 publication-title: New J. Chem. doi: 10.1039/C6NJ03181A contributor: fullname: A Ansari – volume: 60 start-page: 797 year: 2017 ident: 3195_CR11 publication-title: J. Med. Chem. doi: 10.1021/acs.jmedchem.6b01691 contributor: fullname: Y Zafrani – volume: 97 start-page: 786 year: 2015 ident: 3195_CR3 publication-title: Eur. J. Med. Chem. doi: 10.1016/j.ejmech.2014.11.059 contributor: fullname: Ş G G Küçükgüzel – ident: 3195_CR8 doi: 10.1002/ejoc.201500258 – volume: 114 start-page: 2432 year: 2014 ident: 3195_CR10 publication-title: Chem. Rev. doi: 10.1021/cr4002879 contributor: fullname: J Wang – volume: 55 start-page: 52 year: 2019 ident: 3195_CR20 publication-title: Chem. Heterocycl. Compd. doi: 10.1007/s10593-019-02418-4 contributor: fullname: Y V Burgart – volume: 186 start-page: 28 year: 2016 ident: 3195_CR19 publication-title: J. Fluorine Chem. doi: 10.1016/j.jfluchem.2016.04.009 contributor: fullname: D N Bazhin – volume: 47 start-page: 904 year: 2011 ident: 3195_CR17 publication-title: Russ. J. Org. Chem. doi: 10.1134/S1070428011060121 contributor: fullname: O G Khudina – ident: 3195_CR2 doi: 10.3998/ark.5550190.p008.131 – volume: 178 start-page: 306 year: 2015 ident: 3195_CR7 publication-title: J. Fluorine Chem. doi: 10.1016/j.jfluchem.2015.08.015 contributor: fullname: K Kaur – volume: 131 start-page: 1071 year: 2010 ident: 3195_CR9 publication-title: J. Fluorine Chem. doi: 10.1016/j.jfluchem.2010.03.003 contributor: fullname: D O’Hagan – volume: 84 start-page: 107 year: 1997 ident: 3195_CR16 publication-title: J. Fluorine Chem. doi: 10.1016/S0022-1139(97)00054-7 contributor: fullname: V I Saloutin – volume: 88 start-page: 425 year: 2019 ident: 3195_CR12 publication-title: Russ. Chem. Rev. doi: 10.1070/RCR4871 contributor: fullname: L V Politanskaya – volume: 121 start-page: 3 year: 2021 ident: 3195_CR6 publication-title: Chem. Rev. doi: 10.1021/acs.chemrev.0c01015 contributor: fullname: P K Mykhailiuk – volume: 59 start-page: 1967 year: 2010 ident: 3195_CR18 publication-title: Russ. Chem. Bull. doi: 10.1007/s11172-010-0341-7 contributor: fullname: O G Khudina – volume: 24 start-page: 349 year: 2006 ident: 3195_CR15 publication-title: J. Mol. Graph. Model. doi: 10.1016/j.jmgm.2005.09.008 contributor: fullname: M Vega-Teijido – volume: 113 start-page: 145 year: 2016 ident: 3195_CR4 publication-title: Eur. J. Med. Chem. doi: 10.1016/j.ejmech.2016.02.030 contributor: fullname: D Havrylyuk – volume: 64 start-page: 112 year: 2008 ident: 3195_CR21 publication-title: Acta Crystallogr., Sect. A: Found. Crystallogr. doi: 10.1107/S0108767307043930 contributor: fullname: G M Sheldrick |
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| SubjectTerms | Chemistry Chemistry and Materials Science Chemistry/Food Science Diketones Full Articles Inorganic Chemistry Methylhydrazine Organic Chemistry Reagents Regioselectivity Sodium nitrite Synthesis |
| Title | Alternative approaches to the synthesis of polyfluoroalkyl-containing 1-methyl-4-nitrosopyrazoles |
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