RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml
PDF herunterladen
CC BY-NC-ND 4.0 · Synthesis 2023; 55(08): 1221-1226
DOI: 10.1055/s-0042-1751401
DOI: 10.1055/s-0042-1751401
paper
An Efficient Catalyst-Free Direct Approach to 5-Polyfluoroalkyl-1,2,4-triazole-3-thiones
Autoren
This study was partially supported by the Ministry of Education and Science of Ukraine (State Budget Projects 0119U100232 and 0120U100431).
Abstract
An easy to handle high-efficient approach to 5-polyfluoroalkyl-1,2,4-triazole-3-thiones (11 examples, up to 91% yield) is reported. The tautomerism of thione and thiol forms for the obtained products is discussed. A one step procedure for 6,6-dimethyl-3-(trifluoromethyl)-5,6-dihydro[1,3]thiazolo[2,3-c][1,2,4]triazole formation from trifluoroacetic acid and 4-methallylthiosemicarbazide has been developed. The structures of the products were unambiguously determined by complex NMR investigation and by single crystal X-ray diffraction.
Key words
thiosemicarbazide - perfluorocarboxylic acid - 1,2,4-triazol-3-thione - fluoroalkyl - [1,3]thiazolo[2,3-c][1,2,4]triazole - electrophilic cyclizationSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0042-1751401.
- Supporting Information (PDF) (opens in new window)
Publikationsverlauf
Eingereicht: 02. Januar 2022
Angenommen nach Revision: 28. November 2022
Artikel online veröffentlicht:
05. Januar 2023
© 2023. The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution-NonDerivative-NonCommercial-License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by-nc-nd/4.0/)
Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany
-
References
- 1a Kucukguzel S, Cikla-Suzgun P. Eur. J. Med. Chem. 2015; 97: 830
- 1b Korol N, Slivka M. Chem. Heterocycl. Comp. 2017; 53: 852
- 1c Sathyanarayana R, Poojary B. J. Chin. Chem. Soc. 2020; 1
- 1d Song M.-X, Deng X.-Q. J. Enzym. Inhib. Med. Chem. 2018; 33: 453
- 1e Aggarwal R, Sumran G. Eur. J. Med. Chem. 2020; 205: 112652
- 1f Slivka MV, Korol NI, Fizer MM. J. Heterocycl. Chem. 2020; 57: 3236
- 2a Barbuceanu S, Draghici C, Barbuceanu F, Bancescu G, Saramet G. Chem. Pharm. Bull. 2015; 63: 694
- 2b Saundane A, Manjunatha Y. Arab. J. Chem. 2016; 9: S501
- 2c Tratat C, Haroun M, Paparisva A, Geronikaki A, Kamoutsis Ch, Ciric A, Glamoclija J, Sokovic M, Fotakis Ch, Zoumpoulakis P, Bhunia SS, Saxena AK. Arab. J. Chem. 2018; 11: 573
- 2d Slivka MV, Korol NI, Pantyo V, Baumer VM, Lendel VG. Heterocycl. Commun. 2017; 23: 109
- 2e Fizer M, Sukharev S, Slivka M, Mariychuk R, Lendel V. J. Organomet. Chem. 2016; 804: 6
- 3a Naseer MdA, Husain A. J. Drug Deliv. Ther 2019; 9: 236
- 3b Sarigol D, Uzgoren-Baran A, Tel B, Somuncuoglu E, Kazkayasi I, Ozadali-Sari K, Unsal-Tan O, Okay G, Ertan M, Tozkoparan B. Bioorg. Med. Chem. 2015; 23: 2518
- 3c Cristina A. Farmacia 2018; 66: 883
- 3d Toma A, Mogoşan C, Vlase L, Leonte D, Zaharia V. Med. Chem. Res. 2017; 26: 2602
- 4 Khan I, Khan A, AhsanHalim S, Saeed A, Mehsud S, Csuk R, Al-Harrasi A, Ibrar A. Int. J. Biol. Macromol. 2020; 142: 345
- 5 Fizer M, Slivka M, Fizer O. Biointer. Res. Appl Chem. 2021; 6: 13885
- 6a Piccionello AP, Pibiri I, Buscemi S, Pace A. Fluorine in Life Sciences: Pharmaceuticals, Medicinal Diagnostics, and Agrochemicals . Elsevier Inc; Amsterdam: 2019: 213
- 6b Nenajdenko V. Fluorine in Heterocyclic Chemistry . Springer; Cham: 2014
- 7a Inoue M, Sumii Y, Shibata N. ACS Omega 2020; 5: 10633
- 7b Ogawa Y, Tokunaga E, Kobayashi O, Hirai K, Shibata N. iScience 2020; 23: 101467
- 8 Mlostoń G, Obijalska E, Żurawik A, Heimgartner H. Chem. Heterocycl. Comp. 2016; 52: 133
- 9 Frackenpohl J, Schneider L, Decker L, Dittgen J, Fenkl F, Fischer C, Franke J, Freigang J, Getachew R, Gonzalez F.-N, Susana M, Helmke H, Hills MJ, Hohmann S, Kleemann J, Kurowski K, Lange G, Luemmen P, Meyering N, Poree F, Schmutzler D, Wrede S. Bioorg. Med. Chem. 2019; 27: 115142
- 10 Ashton WT, Cantone CL, Chang LL, Hutchine SM, Strelitz RA, MacCoss M, Chang RS. L, Lotti VJ, Faust KA, Chen T.-B, Bunting P, Schorn TW, Kivlighn SD, Siegl PK. S. J. Med. Chem. 1993; 36: 591
- 11 Vasil'eva EB, Sevenard DV, Khomutov OG, Kuznetsova OA, Karpenko NS, Filyakova VI. Russ. J. Org. Chem. 2004; 40: 874
- 12 Vasil’eva EB, Filyakova VI, Sidorova LP, Filatov IE, Charushin VN. Russ. J. Org. Chem. 2005; 41: 1522
- 13a Erdman DT. Patent US6472535, 2002
- 13b Watanabe Y, Mihara J, Yamazaki D, Shibuya K, Shimojo E, Emoto A. Patent EP 2006/002262, 2006
- 13c Michot C. Patent US7919629, 2011
- 13d Linker K.-H, Haas W, Findeisen K, Diehr H.-J. Patent EP 0661277A1, 1994
- 14 Faridoon Hussein WM, Vella P, Islam NU, Ollis DL, Schenk D, McGeary RP. Bioorg. Med. Chem. Lett. 2012; 22: 380
- 15 Ashton WT, Cantone CL, Meurer LC, Tolman RL, Greenlee WJ, Patchett AA, Lynch RJ, Schorn TW, Strouse JF, Siegl PK. S. J. Med. Chem. 1992; 35: 2103
- 16a Fizer M, Slivka M, Sidey V, Baumer V, Fizer O. J. Mol. Struct. 2021; 1241: 130632
- 16b Korol N, Slivka M, Fizer M, Baumer V, Lendel V. Monatsh. Chem. 2020; 151: 191
- 17a El Ashry ES. H, Awad LF, Soliman SM, Al Moaty MN. A, Ghabbour HA, Barakat A. J. Mol. Struct. 2017; 1146: 432
- 17b Özdemir N, Türkpençe D. Comput. Theor. Chem. 2013; 1025: 35
- 17c Davari MD, Bahrami H, Haghighi ZZ, Zahedi M. J. Mol. Model. 2021; 16: 841
- 18a Danilkina NA, Kulyashova AE, Khlebnikov AF, Bräse S, Balova IA. J. Org. Chem. 2014; 79: 9018
- 18b Andrade VS, Mattos MC. Synthesis 2019; 51: 1841
- 18c D’Hollander AC. A, Peilleron L, Grayfer TD, Cariou K. Synthesis 2019; 51: 1753
- 18d Slivka M, Onysko M. Synthesis 2021; 53: 3497
- 19 Fizer M, Slivka M, Baumer V. J. Organomet. Chem. 2021; 952: 122044
- 20 CCDC 2026192 (8) contains the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/structures
- 21 Fizer MM, Slivka MV, Lendel VG. Chem. Heterocycl. Compd. 2019; 55: 478
- 22a Sheldrick GM. Acta Crystallogr., Sect. C 2015; 71: 3
- 22b Sheldrick GM. Acta Crystallogr., Sect. A 2015; 71: 3
- 23 Farrugia LJ. J. Appl. Crystallogr. 1999; 32: 837