Skip to main content
SpringerLink
Log in

[3+2] Cycloaddition reactions of 1-substituted 3,3,3-trifluoropropenes with diazo compounds and nitrilimines – synthesis of pyrazolines and pyrazoles

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

1,3-Dipolar cycloaddition reactions of 3,3,3-trifluoropropene derivatives containing a sulfonyl, sulfamide, or sulfoximine substituent in position 1 with diazomethane proceed with the formation of 3-substituted 4-(trifluoromethyl)-4,5-dihydro-1H-pyrazoles and 3-(trifluoromethyl)-1H-pyrazole, whereas reactions with ethyl diazoacetate and 2,2,2-trifluorodiazoethane lead to the formation of isomeric 5(3)-substituted 4-trifluoromethyl-3,4(4,5)-dihydro-2(1)H-pyrazoles and 4-substituted 5-(trifluoromethyl)-4,5-dihydro-1Hpyrazoles, the stability of which depends on the nature of the heteroatomic substituent. The cycloaddition of 1-sulfonyl- and 1-sulfamoylsubstituted derivatives of 3,3,3-trifluoropropene to C-carbethoxy-N-phenylnitrilimine gives rise to 4-substituted ethyl 1-phenyl-5-(trifluoromethyl)-4,5-dihydro-1H-pyrazole-3-carboxylates and ethyl 1-phenyl-4-(trifluoromethyl)-1H-pyrazole-3-carboxylate.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Subscribe and save

Springer+ Basic
$34.99 /Month
  • Get 10 units per month
  • Download Article/Chapter or eBook
  • 1 Unit = 1 Article or 1 Chapter
  • Cancel anytime
Subscribe now

Buy Now

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Figure 1.

Similar content being viewed by others

Notes

  1. Hereinafter in the experimental part, the signals of the major isomer are marked with an asterisk (*), the signals of both isomers are marked with two asterisks (**).

References

  1. (a) Faria, J. V.; Vegi, P. F.; Miguita, A. G .C.; dos Santos, M. S.; Boechat, N.; Bernardino, A. M. R. Bioorg. Med. Chem. 2017, 25, 5891. (b) Faisal, M.; Saeed, A.; Hussain, S.; Dar, P.; Larik, F. A. J. Chem. Sci. 2019, 131, 70. (c) Schmidt, A.; Dreger, A. Curr. Org. Chem. 2011, 15, 1423.

  2. (a) Kumar, S.; Bawa, S.; Drabu, S.; Kumar, R.; Gupta, H. Recent Pat. Anti-Infect. Drug Discovery 2009, 4, 154. (b) Turkan, F.; Cetin, A.; Taslimi, P.; Karaman, H. S.; Gulçin, I. Arch. Pharm. 2019, 352, 1800359. (c) Azarifar, D.; Shaebanzadeh, M. Molecules 2002, 7, 885. (d) Malhotra, V.; Pathak, S.; Nath, R.; Mukerjee, D.; Shanker, K. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 2002, 41B, 1310. (e) Palaska, E.; Aytemir, M.; Uzbay, T.; Eros, D. Eur. J. Med. Chem. 2001, 36, 639.

  3. (a) Penning, T. D.; Talley, J. J.; Bertenshaw, S. R.; Carter, J. S.; Collins, P. W.; Docter, S.; Graneto, M. J.; Lee, L. F.; Malecha, J. W.; Miyashiro, J. M.; Rogers, R. S.; Rogier, D. J.; Yu, S. S.; Anderson, G. D.; Burton, E. G.; Cogburn, J. N.; Gregory, S. A.; Koboldt, C. M.; Perkins, W. E.; Seibert, K.; Veenhuizen, A. W.; Zhang, Y. Y.; Isakson, P. C. J. Med. Chem. 1997, 40, 1347. (b) Sun, A.; Chandrakumar, N.; Yoon, J.-J.; Plemper, R. K.; Snyder, J. P. Bioorg. Med. Chem. Lett. 2007, 17, 5199. (c) Quan, M. L.; Lam, P. Y. S.; Han, Q.; Pinto, D. J. P.; He, M. Y., Li, R.; Ellis, C. D.; Clark, C. G.; Teleha, C. A.; Sun, J.-H.; Alexander, R. S.; Bai, S.; Luettgen, J. M.; Knabb, R. M.; Wong, P. C.; Wexler, R. R. J. Med. Chem. 2005, 48, 1729. (d) Giornal, F.; Pazenok, S.; Rodefeld, L.; Lui, N.; Vors, J.-P.; Leroux, F. R. J. Fluorine Chem. 2013, 152, 2. (e) Foster, R. S.; Jakobi, H.; Harrity, J. P. A. Org. Lett. 2012, 14, 4858. (f) Topchij, M. A.; Zharkova, D. A.; Asachenko, A. F.; Muzalevskiy, V. M.; Chertkov, V. A.; Nenajdenko, V. G.; Nechaev, M. S. Eur. J. Org. Chem. 2018, 27-28, 3750. (g) Muzalevskiy, V. M.; Nenajdenko, V. G. Org. Biomol. Chem. 2018, 16, 7935. (h) Wang, H.; Ning, Y.; Sun, Y.; Sivaguru, P.; Bi, X. Org. Lett. 2020, 22, 2012. (i) Pianoski, K. E.; Poletto, J.; da Silva, M. J. V.; Camargo, J. N. A.; Jacomini, A. P.; Gonçalves, D. S.; Back, D. F.; Moura, S.; Rosa, F. A. Org. Biomol. Chem. 2020, 18, 2524. (j) Zeng, H.; Fang, X.; Yang, Z.; Zhu, C.; Jiang, H. J. Org. Chem. 2021, 86, 2810.

  4. (a) Markitanov, Yu. N.; Timoshenko, V. M.; Shermolovich, Yu. G.; Mykhalchuk, V. L.; Grafova, I. A.; Grafov, A. V. Chem. Heterocycl. Compd. 2016, 52, 503. [Khim. Geterotsikl. Soedin. 2016, 52, 503.] (b) Markitanov, Yu. M.; Timoshenko, V. M.; Shermolovich, Yu. G. Chem. Heterocycl. Compd. 2018, 54, 89. [Khim. Geterotsikl. Soedin. 2018, 54, 89.] (c) Markitanov, Yu. M.; Timoshenko, V. M.; Rudenko, T. V.; Rusanov, E. B.; Shermolovich, Yu. G. J. Sulfur Chem. 2019, 40, 629. b Markitanov, Yu. N.; Timoshenko, V. M.; Rusanov, E. B.; Shermolovich, Yu. G. Chem. Heterocycl. Compd. 2021, 57, 253. [Khim. Geterotsikl. Soedin. 2021, 57, 253.]

  5. (a) Smith, L. I.; Davis, H. R. J. Org. Chem. 1950, 15, 824. (b) Rondestvedt, C. S.; Chang, P. K. J. Am. Chem. Soc. 1955, 77, 6532. (c) Reddy, N.; Balaji, T. S. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 1984, 23B, 983. (d) Kumar, A.; Sharma, A., S.; Malik, N.; Sharma, P.; Kaushik, K.; Saxena, K. K.; Srivastava, V. K. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 2004, 43B, 1532.

  6. Vasin, V. A.; Razin, V. V.; Bezrukova, E. V.; Korovin, D. Yu.; Petrov, P. S.; Somov, N. V. Russ. J. Org. Chem. 2015, 51, 1144. [Zh. Org. Khim. 2015, 51, 1163.]

  7. (a) Hock, K. J.; Mertens, L.; Metze, F. K.; Schmittmann, C.; Koenigs, R. M. Green Chem. 2017, 19, 905. (b) Britton, J.; Jamison, T. F. Angew. Chem., Int. Ed. 2017, 56, 8823. (с) Mertens, M.; Hock, K. J.; Koenigs, R. M. Chem.–Eur. J. 2016, 22, 9542. c Li, F.; Nie, J.; Sun, L.; Zheng, Y.; Ma, J.-A. Angew. Chem., Int. Ed. 2013, 52, 6255. d Li, F.; Wang, J.; Pei, W.; Li, H.; Zhang, H.; Song, M.; Guo, L.; Zhang, A.; Liu, L. Tetrahedron Lett. 2017, 58, 4344. e Mei, H.; Wang, L.; Pajkert R.; Wang, Q.; Xu, J.; Liu, J.; Röschenthaler, G.-V.; Han, J. Org. Lett. 2021, 23, 1130.

  8. Minami, T.; Tokumasu, S.; Mimasu, R.; Hirao, I. Chem. Lett. 1985, 14, 1099.

  9. Gareev, R. D.; Pudovik, A. N. J. Gen. Chem. USSR 1982, 52, 2333. [Zh. Obshch. Khim. 1982, 52, 2637.]

  10. Matoba, K.; Yonemoto, H.; Fukui, M.; Yamazaki, T. Chem. Pharm. Bull. 1984, 32, 3918.

  11. (a) Berestovitskaya, V. M.; Anisimova, N. A.; Gubaidullin, A. T.; Litvinov, I. A.; Berkova, G. A.; Makarova, N. G. Russ. J. Gen. Chem. 2009, 79, 1446. [Zh. Obsh. Khim. 2009, 79, 1090.] (b) Berkova, G. A.; Anisimova, N. A.; Makarova, N. G.; Deiko, L. I.; Berestovitskaya, V. M. Russ. J. Gen. Chem. 2006, 76, 153. [Zh. Obsh. Khim. 2006, 76, 156.]

  12. Plancquaert, M.-A.; Redone, M.; Janousek, Z.; Viehe, H. G. Tetrahedron 1996, 52, 4383.

  13. (а) Yu, H.-B.; Huang, W.-Y. J. Fluorine Chem. 1998, 87, 69. a Gerus, I. I.; Gorbunova M. G.; Vdovenko, S. I.; Yagupol’skii, Yu. L.; Kukhar, V. P. J. Org. Chem. USSR 1990, 26, 1623. [Zh. Org. Khim. 1990, 26, 1877.] (c) Jiang, B.; Xu, Y.-Y.; Yang, J. J. Fluorine Chem. 1994, 67, 83. b Atherton, J. H.; Fields, R. J. Chem. Soc. C 1968, 1507. c Petrella, S.; Aubry, A.; Janvier, G.; Coutant, E. P.; Cartier, A.; Dao, T.-H.; Bonhomme, F. J.; Motreff, L.; Pissis, C.; Bizet, C.; Clermont, D.; Begaud, E.; Retailleau, P.; Munier-Lehmann, H.; Capton, E.; Mayer, C.; Janin, Y. L. Can. J. Chem. 2015, 94, 240.

  14. (a) Muruganantham, R.; Namboothiri, I. N. N. J. Org. Chem. 2010, 75, 2197. (b) Muruganantham, R.; Mobin, S. M.; Namboothiri, I. N. N. Org. Lett. 2007, 9, 1125.

  15. Slobodyanyuk, E. V.; Artamonov, O. S.; Shishkin, O. V.; Mykhailiuk, P. K. Eur. J. Org. Chem. 2014, 12, 2487.

  16. Janin, Y. L. J. Heterocycl. Chem. 2013, 50, 1410.

  17. (a) Kobayashi, Y.; Hamana, H.; Fujino, S.; Ohsawa, A.; Kumadaki, I. J. Org. Chem. 1979, 44, 4930. (b) Gerus, I. I.; Mironetz, R. X.; Kondratov, I. S.; Bezdudny, A. V.; Dmytriv, Y. V.; Shishkin, O. V.; Starova, V. S.; Zaporozhets, O. A.; Tolmachev, A. A.; Mykhailiuk, P. K. J. Org. Chem. 2012, 77, 47.

  18. (a) Elguero, J.; Yranzo, G. I.; Laynez, J.; Jimenez, P.; Menendez, M.; Catalan, J.; De Paz, J. L. G.; Anvia, F.; Taft, R. W. J. Org. Chem. 1991, 56, 3942. (b) Claire, P. P. K.; Coe, P. L.; Jones, C. J.; McCleverly, J. A. J. Fluorine Chem. 1991, 51, 283. (с) Grünebaum, M.; Buchheit, A.; Günther, C.; Wiemhöfer, H.-D. Tetrahedron Lett. 2016, 57, 1555. c Maspero, A.; Giovenzana, G. B.; Monticelli, D.; Tagliapietra, S.; Palmisano, G.; Penoni, A. J. Fluorine Chem. 2012, 139, 53. d Kondrat’ev, P. N.; Skryabina, Z. E.; Saloutin, V. I.; Pashkevich, K. I.; Klyuev, N. A.; Aleksandrov, G. G. Bull. Acad. Sci. USSR., Div. Chem. Sci. 1990, 39, 561. [Izv. Akad. Nauk SSSR, Ser. Khim. 1990, 640.]

  19. (a) Shawali, A. S.; Albar, H. A. Can. J. Chem. 1986, 64, 871. (b) Kulikov, A. S.; Epishina, M. A.; Zhilin, E. S.; Shuvaev, A. D.; Fershtat, L. L.; Makhova, N. N. Mendeleev Commun. 2021, 31, 42.

  20. (a) Zeng, H.; Fang, X.; Yang, Z.; Zhu, C.; Jiang, H. J. Org. Chem. 2021, 86, 2810. (b) Saloutin, V. I.; Skryabina, Z. E.; Kondrat’ev, P. N.; Perevalov, S. G. Russ. J. Org. Chem. 1995, 31, 236. [Zh. Org. Khim. 1995, 31, 266.]

  21. Nickson, T. E. J. Org. Chem. 1988, 53, 3870.

  22. Arndt, F. Org. Synth. 1935, 15, 3.

  23. Sheldrick, G. M. Acta Crystallogr., Sect. A: Found. Crystallogr. 2008, A64, 112.

Download references

Author information

Authors and Affiliations

  1. Institute of Organic Chemistry, National Academy of Sciences of Ukraine, 5 Murmanska St., Kyiv, 02660, Ukraine

    Yuriy N. Маrkitanov, Vadim М. Тimoshenko, Sergiy S. Мykhaylychenko, Eduard B. Rusanov & Yuriy G. Shermolovich

  2. L. M. Litvinenko Institute of Physical-Organic Chemistry and Coal Chemistry, National Academy of Sciences of Ukraine, 50 Kharkivske Shose, Kyiv, 02160, Ukraine

    Alexandr I. Khyzhan

  3. Enamine Ltd., 78 Chervonotkatska St., Kyiv, 02094, Ukraine

    Alexandr I. Khyzhan

Authors
  1. Yuriy N. Маrkitanov
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Vadim М. Тimoshenko
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Sergiy S. Мykhaylychenko
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Eduard B. Rusanov
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Alexandr I. Khyzhan
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Yuriy G. Shermolovich
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Vadim М. Тimoshenko.

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2021, 57(11), 1107–1115

Supplementary Information

ESM 1

(PDF 2504 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Маrkitanov, Y.N., Тimoshenko, V.М., Мykhaylychenko, S.S. et al. [3+2] Cycloaddition reactions of 1-substituted 3,3,3-trifluoropropenes with diazo compounds and nitrilimines – synthesis of pyrazolines and pyrazoles. Chem Heterocycl Comp 57, 1107–1115 (2021). https://doi.org/10.1007/s10593-021-03029-8

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-021-03029-8

Keywords

Search

Navigation