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1,5-Diarylpent-4-ene-1,3-diones in the synthesis of spiro[(thia)pyrrolizidine-3,3'-oxindoles] and 1,3-diaryl-5-spiro[oxindole-3,3'-pyrrolizidin-2'-yl]-1H-pyrazoles

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Chemistry of Heterocyclic Compounds Aims and scope

The three-component reaction of (E)-1,5-diarylpent-4-ene-1,3-diones, isatins, and (thia)proline in i-PrOH at room temperature proceeds regio- and stereoselectively leading to the formation of spiro[(thia)pyrrolizidine-3,3'-oxindoles] with the 1,3-dicarbonyl moiety in the (thia)pyrrolizidine ring. Subsequent treatment of these tetracyclic products with arylhydrazine hydrochlorides under reflux in the EtOH–AcOH system gave 5-substituted 1,3-diaryl-1H-pyrazoles in high yields.

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References

  1. (a) Arrieta, A.; Beyer, L.; Kleinpeter, E.; Lehmann, J.; Dargatz, M. J. Prakt. Chem. 1992, 334, 696. (b) Reddy, B. P.; Krupadanam, G. L. D. J. Heterocycl. Chem. 1996, 33, 1561. (c) Linn, B. O.; Hauser, C. R. J. Am. Chem. Soc. 1956, 78, 6066.

  2. (a) Jang, Y.-J.; Chen, Y.-S.; Lee, C.-J.; Chen, C.-H.; Lin, W. Synthesis 2015, 95. (b) Chen, C.-H.; Ko, C.-T.; Reddy, G. M.; Lee, C.-J.; Lin, W. Eur. J. Org. Chem. 2015, 5254.

  3. (a) MacDonald, F. K.; Burnell, D. J. J. Org. Chem. 2009, 74, 6973. (b) Saulnier, S.; Lozovskiy, S. V.; Golovanov, A. A.; Ivanov, A. Yu.; Vasilyev, A. V. Eur. J. Org. Chem. 2017, 3635.

  4. (a) Makrandi, J. K.; Kumari, V. Synth. Commun. 1989, 19, 1919. (b) Pinto, J.; Silva, V. L. M.; Silva, A. M. G.; Silva, A. M. S. Molecules 2015, 20, 11418.

  5. Letcher, R. M.; Yue, T.-Y.; Chiu, K.-F.; Kelkar, A. S.; Cheung, K.-K. J. Chem. Soc., Perkin Trans. 1 1998, 3267.

  6. (a) Selvam, C.; Jachak, S. M.; Thilagavathi, R.; Chakraborti, A. K. Bioorg. Med. Chem. Lett. 2005, 15, 1793. (b) Caldarelli, A.; Penucchini, E.; Caprioglio, D.; Genazzani, A. A.; Minassi, A. Bioorg. Med. Chem. 2013, 21, 5510. (c) Nieto, C. I.; Cabildo, M. P.; Cornago, M. P.; Sanz, D.; Claramunt, R. M.; Torralba, M. C.; Torres, M. R.; Elguero, J.; García, J. A.; López, A.; Acuña-Castroviejo, D. Molecules 2015, 20, 15643.

  7. (a) Liou, Y.-C.; Su, Y.-H.; Ku, K.-C.; Edukondalu, A.; Lin, C.-K.; Ke, Y.-S.; Karanam, P.; Lee, C.-J.; Lin, W. Org. Lett. 2019, 21, 8339. (b) Sousa, J. L. C.; Talhi, O.; Rocha, D. H. A.; Pinto, D. C. G. A.; Paz, F. A. A.; Bachari, K.; Kirsch, G.; Silva, A. M. S. Synlett 2015, 2724.

  8. (a) Nájera, C.; Sansano, J. M. Pure Appl. Chem. 2019, 91, 575. (b) Mei, G.-J.; Shi, F. Chem. Commun. 2018, 54, 6607. (c) Döndas, H. A.; de Gracia Retamosa, M.; Sansano, J. M. Synthesis 2017, 2819. (d) Pavlovska, T. L.; Redkin, R. Gr.; Lipson, V. V.; Atamanuk, D. V. Mol. Diversity 2016, 20, 299. (e) Yan, L.-J.; Wang, Y.-C. ChemistrySelect 2016, 1, 6948. (f) Lashgari, N.; Ziarani, G. M. ARKIVOC 2012, (i), 277. (g) Zhou, L.-M.; Qu, R.-Y.; Yang, G.-F. Expert Opin. Drug Discovery 2020, 15, 603. (h) Ye, N.; Chen, H.; Wold, E. A.; Shi, P. Y.; Zhou, J. ACS Infect. Dis. 2016, 2, 382. (i) Yu, B.; Yu, D.-Q.; Liu, H.-M. Eur. J. Med. Chem. 2015, 97, 673. (j) Santos, M. M. M. Tetrahedron 2014, 70, 9735. (k) Beloglazkina, A. A.; Karpov, N. A.; Mefedova, S. R.; Polyakov, V. S.; Skvortsov, D. A.; Kalinina, M. A.; Tafeenko, V. A.; Majouga, A. G.; Zyk, N. V.; Beloglazkina, E. K. Russ. Chem. Bull., Int. Ed. 2019, 68, 1006. [Izv. Akad. Nauk, Ser. Khim. 2019, 1006.]

  9. (a) Jossang, A.; Jossang, P.; Hadi, H. A.; Sévenet, T.; Bodo, B. J. Org. Chem. 1991, 56, 6527. (b) Kornet, M. J.; Thio, A. P. J. Med. Chem. 1976, 19, 892. (c) Kang, T.-H.; Murakami, Y.; Takayama, H.; Kitajima, M.; Aimi, N.; Watanabe, H.; Matsumoto, K. Life Sci. 2004, 76, 331. (d) Kathirvelan, D.; Haribabu, J.; Reddy, B. S. R.; Balachandran, C.; Duraipandiyan, V. Bioorg. Med. Chem. Lett. 2015, 25, 389. (e) Barakat, A.; Islam, M. S.; Ghawas, H. M.; Ghawas, H. M.; Al-Majid, A. M.; El-Senduny, F. F.; Badria, F. A.; Elshaier, Y. A. M. M.; Ghabbour, H. A. Bioorg. Chem. 2019, 86, 598.

  10. Zimnitskiy, N. S.; Denikaev, A. D.; Barkov, A. Y.; Kutyashev, I. B.; Korotaev, V. Y.; Sosnovskikh, V. Y. J. Org. Chem. 2020, 85, 8683.

    Article  CAS  Google Scholar 

  11. (a) Barkov, A. Yu.; Zimnitskiy, N. S.; Korotaev, V. Yu.; Kutyashev, I. B.; Moshkin, V. S.; Sosnovskikh, V. Ya. Tetrahedron 2016, 72, 6825. (b) Kutyashev, I. B.; Barkov, A. Yu.; Korotaev, V. Yu.; Sosnovskikh, V. Ya. Chem. Heterocycl. Compd. 2019, 55, 529. [Khim. Geterotsikl. Soedin. 2019, 55, 529.] (c) Kutyashev, I. B.; Ulitko, M. V.; Barkov, A. Yu.; Zimnitskiy, N. S.; Korotaev, V. Yu.; Sosnovskikh, V. Ya. New J. Chem. 2019, 43, 18495. c Kutyashev, I. B.; Kochnev, I. A.; Cherepkova, A. A.; Zimnitskiy, N. S.; Barkov, A. Yu.; Korotaev, V. Yu.; Sosnovskikh, V. Ya. Chem. Heterocycl. Compd. 2020, 56, 1302. [Khim. Geterotsikl. Soedin. 2020, 56, 1302.]

  12. Izmest'ev, A. N.; Gazieva, G. А.; Kravchenko, A. N. Chem. Heterocycl. Compd. 2020, 56, 255. [Khim. Geterotsikl. Soedin. 2020, 56, 255.]

  13. Sheldrick, G. M. Acta Crystallogr., Sect. A: Found. Crystallogr. 2015, A71, 3.

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Authors and Affiliations

  1. Institute of Natural Sciences and Mathematics of Ural Federal University named after the first President of Russia B. N. Yeltsin, 51 Lenin Ave, Yekaterinburg, 620000, Russia

    Vladislav Yu. Korotaev, Nikolay S. Zimnitskiy, Andrey D. Denikaev, Alexey Yu. Barkov, Igor B. Kutyashev & Vyacheslav Ya. Sosnovskikh

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  1. Vladislav Yu. Korotaev
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  2. Nikolay S. Zimnitskiy
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  3. Andrey D. Denikaev
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  4. Alexey Yu. Barkov
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  5. Igor B. Kutyashev
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  6. Vyacheslav Ya. Sosnovskikh
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Correspondence to Vladislav Yu. Korotaev.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2021, 57(1), 81–91

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Korotaev, V.Y., Zimnitskiy, N.S., Denikaev, A.D. et al. 1,5-Diarylpent-4-ene-1,3-diones in the synthesis of spiro[(thia)pyrrolizidine-3,3'-oxindoles] and 1,3-diaryl-5-spiro[oxindole-3,3'-pyrrolizidin-2'-yl]-1H-pyrazoles. Chem Heterocycl Comp 57, 81–91 (2021). https://doi.org/10.1007/s10593-021-02871-0

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