Three-component synthesis of fluorinated pyrazoles from fluoroalkylamines, NaNO2 and electron-deficient alkynes

Organic and Biomolecular Chemistry

Volumn 13, Issue 11, 2015, Pages 3438-3445

  Mykhailiuk, Pavel K ^a,b  

^a ENAMINE LTD   (Ukraine)

^b TARAS SHEVCHENKO NATIONAL UNIVERSITY OF KYIV   (Ukraine)

Author keywords

[No Author keywords available]

Indexed keywords

CHLORINE COMPOUNDS; HYDROCARBONS; SODIUM COMPOUNDS;

ELECTRON-DEFICIENT; FLUORINATED PYRAZOLES; FLUORINE ATOMS; FLUOROALKYL GROUP; HIGH YIELD; THREE COMPONENT; THREE COMPONENT REACTIONS;

NITROGEN COMPOUNDS;

ALKYNE; AMINE; FLUORINATED HYDROCARBON; PYRAZOLE DERIVATIVE; SODIUM NITRITE;

CHEMICAL STRUCTURE; CHEMISTRY; ELECTRON; SYNTHESIS;

ALKYNES; AMINES; ELECTRONS; HYDROCARBONS, FLUORINATED; MOLECULAR STRUCTURE; PYRAZOLES; SODIUM NITRITE;

EID: 84924326277     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/c4ob02670e     Document Type: Article

References (57)

1. Fluorinated Heterocyclic Compounds: Synthesis, Chemistry and Applications, ed., V. A. Petrov, John Wiley & Sons, Inc., Publishers, New Jersey, 2009
2. Bioorganic and Medicinal Chemistry of Fluorine, ed., J.-P. Bégué, and, D. Bonnet-Delpon, John Wiley & Sons, New Jersey, 2008
3. Fluorine in Medicinal Chemistry and Chemical Biology, ed., I. Ojima, Blackwell Publishing, 2009
4. Fluorine in Pharmaceutical and Medicinal Chemistry: From Biophysical Aspects to Clinical Applications, ed., V. Gouverneur, and, K. Müller, Imperial College Press, London, 2012
5. J. Wang M. Sánchez-Roselló J. L. Aceña C. del Pozo A. E. Sorochinsky S. Fusteero V. A. Soloshonok H. Liu Chem. Rev. 2014 114 2432
6. T. Fujiwara D. O'Hagan J. Fluorine Chem. 2014 167 16
7. D. O'Hagan J. Fluorine Chem. 2010 131 1071
8. S. Purser P. R. Moore S. Swallow V. Gouverneur Chem. Soc. Rev. 2008 37 320
9. W. K. Hagmann J. Med. Chem. 2008 51 4359
10. For reviews on fluorinated pyrazoles, see: S. Fustero M. Sanchez-Rosello P. Barrio A. Simon-Fuentes Chem. Rev. 2011 111 6984
11. F. Giornal S. Pazenok L. Rodefeld N. Lui J.-P. Vors F. R. Leroux J. Fluorine Chem. 2013 152 2
12. S. Fustero A. Simon-Fuentes J. F. Sanz-Cervera Org. Prep. Proced. Int. 2009 41 253
13. For some recent papers on fluoroalkyl pyrazoles, see: Q. Sha H. Liu Y. Wei Eur. J. Org. Chem. 2014 7707
14. R. T. Iminov A. V. Mashkov I. I. Vyzir B. A. Chalyk A. V. Tverdokhlebov P. K. Mykhailiuk L. N. Babichenko A. A. Tolmachev Y. M. Volovenko A. Biitseva O. V. Shishkin S. V. Shishkina Eur. J. Org. Chem. 2015 886
15. F. Giornal G. Landelle N. Lui J.-P. Vors S. Pazenok F. R. Leroux Org. Process Res. Dev. 2014 18 1002
16. R. Roman A. Navarro D. Wodka M. Alvim-Gaston S. Husain N. Franklin A. Simón-Fuentes S. Fustero Org. Process Res. Dev. 2014 18 1027
17. S. Pazenok F. Giornal G. Landelle N. Lui J.-P. Vors F. R. Leroax Eur. J. Org. Chem. 2013 4249
18. I. I. Gerus R. X. Mironetz I. S. Kondratov A. V. Bezdudny Y. V. Dmytriv O. V. Shishkin V. S. Starova O. A. Zaporozhets A. A. Tolmachev P. K. Mykhailiuk J. Org. Chem. 2012 77 47
19. Some reviews on fluoroalkylation, see: J.-A. Maa D. Cahard Chem. Rev. 2004 104 6119
20. Y. Macé E. Magnier Eur. J. Org. Chem. 2012 2479
21. C. Ni M. Hu J. Hu Chem. Rev. 2015 115 765
22. O. A. Tomashenko V. V. Gruushin Chem. Rev. 2011 111 4475
23. J. Charpentier N. Früh A. Togni Chem. Rev. 2015 115 650
24. S. Barata-Vallejo B. Lantano A. Postigo Chem. - Eur. J. 2014 20 16806
25. S. Roy B. T. Gregg G. W. Gribble V.-D. Le S. Roy Tetrahedron 2011 67 2161
26. J. Nie H.-C. Guo D. Cahard J.-A. Ma Chem. Rev. 2011 111 455
27. 2 was first described in: H. Gilman R. G. Jones J. Am. Chem. Soc. 1943 65 1458
28. 2 by different research groups: B. Morandi E. M. Carreira Angew. Chem., Int. Ed. 2010 49 938
29. B. Morandi E. M. Carreira Angew. Chem., Int. Ed. 2010 49 4294
30. B. Morandi E. M. Carreira Angew. Chem., Int. Ed. 2011 50 1101
31. F.-G. Zhang Y. Wei Y.-P. Yi J. Nie J.-A. Ma Org. Lett. 2014 16 3122
32. S. Wang J. Nie Y. Zheng J.-A. Ma Org. Lett. 2014 16 1606
33. F. Li J. Nie L. Sun Y. Zheng J.-A. Ma Angew. Chem., Int. Ed. 2013 52 6255
34. O. A. Argintaru D. Ryu I. Aron G. A. Molander Angew. Chem., Int. Ed. 2013 52 13656
35. G. A. Molander L. N. Cavalcanti Org. Lett. 2014 15 3166
36. G. A. Molander D. Ryu Angew. Chem., Int. Ed. 2014 53 14181
37. O. S. Artamonov P. K. Mykhailiuk N. M. Voievoda D. M. Volochnyuk I. V. Komarov Synthesis 2010 443
38. O. S. Artamonov E. Y. Slobodyanyuk O. V. Shishkin I. V. Komarov P. K. Mykhailiuk Synthesis 2013 225
39. O. S. Artamonov E. Y. Slobodyanyuk D. M. Volochnyuk I. V. Komarov A. A. Tolmachev P. K. Mykhailiuk Eur. J. Org. Chem. 2014 3592
40. P. K. Mykhailiuk S. Afonin G. V. Palamarchuk O. V. Shishkin A. S. Ulrich I. V. Komarov Angew. Chem., Int. Ed. 2008 45 5765
41. P. Le Maux S. Juillard G. Simonneaux Synthesis 2006 1701
42. M. A. J. Duncton L. Ayala C. Kaub S. Janagani W. T. Edwards N. Orike K. Ramamoorthy J. Kincaid M. G. Kelly Tetrahedron Lett. 2010 51 1009
43. Z. Chai J.-P. Bouillon D. Caharrd Chem. Commun. 2012 48 9471
44. M. A. J. Duncton R. Singh Org. Lett. 2013 15 4284
45. G. Wu Y. Deng C. Wu X. Wang Y. Zhang J. Wang Eur. J. Org. Chem. 2014 4477
46. T.-R. Li S.-W. Duan W. Ding Y.-Y. Liu J.-R. Chen L.-Q. Lu W.-J. Xiao J. Org. Chem. 2014 79 2296
47. E. Y. Slobodyanyuk O. S. Artamonov O. V. Shishkin P. K. Mykhailiuk Eur. J. Org. Chem. 2014 2487
48. P. K. Mykhailiuk Beilstein J. Org. Chem. 2015 11 16
49. P. Mykhailiuk Chem. - Eur. J. 2014 17 4942
50. For a review on [3 + 2]-cycloadditions, see: G. Maas, in Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry toward Heterocycles and Natural Products, ed., A. Padwa, and, W. H. Pearson, Wiley, New York, 2002, pp. 539-621
51. Y. Chiang A. J. Kresge V. V. Popik J. Chem. Soc., Perkin Trans. 2 1999 1107
52. J. H. Atherton R. Fields R. N. Haszeldine J. Chem. Soc. C 1971 366
53. 2 (2.9): C. Hansch A. Leo R. W. Taft Chem. Rev. 1991 91 165
54. For other methods on incorporation of the tetrafluoroethyl group into organic compounds, see: Y. Chernykh K. Hlat-Glembova B. Klepetarova P. Beier Eur. J. Org. Chem. 2011 4528
55. T. M. Sokolenko Y. A. Davydova Y. L. Yagupolskii J. Fluorine Chem. 2012 136 20
56. Y. Chernykh B. Jurasek P. Beier J. Fluorine Chem. 2014 10.1016/j.jfluchem.2014.08.004
57. J. Vaclavik Y. Chernykh B. Jurasek P. Beier J. Fluorine Chem. 2015 169 24