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Base-catalyzed addition of ketones to alkynes as a springboard to cycloalka[c]pyrazoline-2-carbaldehydes

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Chemistry of Heterocyclic Compounds Aims and scope

Unknown cycloalka[c]pyrazoline-2-carbaldehydes are obtained in 52–68% yields when the intermediates of base-catalyzed addition of cyclic ketones to phenylacetylene are treated (without isolation) with hydrazine hydrate in formic acid.

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References

  1. (a) Trofimov, B. A.; Schmidt, E. Yu.; Ushakov, I. A.; Zorina, N. V.; Skital'tseva, E. V.; Protsuk, N. I.; Mikhaleva, A. I. Chem.–Eur. J. 2010, 16, 8516. (b) Trofimov, B. A.; Schmidt, E. Yu.; Zorina, N. V.; Ivanova, E. V.; Ushakov, I. A. J. Org. Chem. 2012, 77, 6880. (c) Trofimov, B. A.; Schmidt, E. Yu.; Zorina, N. V.; Ivanova, E. V.; Ushakov, I. A.; Mikhaleva, A. I. Adv. Synth. Catal. 2012, 354, 1813. (d) Schmidt, E. Yu.; Zorina, N. V.; Tarasova, O. A.; Ushakov, I. A.; Trofimov, B. A. Mendeleev Commun. 2013, 23, 204.

  2. (a) Ohtsuka, Y.; Sasahara, T.; Oishi, T. Chem. Pharm. Bull. 1982, 30, 1106. (b) Gohain, M.; Gogoi, J. B.; Prajapati, D.; Sandhu, J. S. New J. Chem. 2003, 27, 1038. (c) Comprehensive Organic Functional Group Transformations II. Katritzky, A. R.; Taylor, R. J. K. Eds.; Elsevier, 2005, Vol 3, p. 215–266. (d) Iwasaki, M.; Morita, E.; Uemura, M.; Yorimitsu, H.; Oshima, K. Synlett 2007, 167.

  3. Trofimov, B. A.; Schmidt, E. Yu.; Skitaltseva, E. V.; Zorina, N. V.; Protsuk, N. I.; Ushakov, I. A.; Mikhaleva, A. I.; Dyachenko, O. A.; Kazheva, O. N.; Aleksandrov, G. G. Tetrahedron Lett. 2011, 52, 4285.

    Article  CAS  Google Scholar 

  4. Schmidt, E. Yu.; Trofimov, B. A.; Bidusenko, I. A.; Cherimichkina, N. A.; Ushakov, I. A.; Protzuk, N. I.; Gatilov, Y. V. Org. Lett. 2014, 16, 4040.

    Article  CAS  Google Scholar 

  5. Trofimov, B. A.; Schmidt, E. Yu.; Ushakov, I. A.; Mikhaleva, A. I.; Zorina, N. V.; Protsuk, N. I.; Senotrusova, E. Yu.; Skital'tseva, E. V.; Kazheva, O. N.; Aleksandrov, G. G.; Dyachenko, O. A. Eur. J. Org. Chem. 2009, 5142.

  6. Schmidt, E. Yu.; Tatarinova, I. V.; Ivanova, E. V.; Zorina, N. V.; Ushakov, I. A.; Trofimov, B. A. Org. Lett. 2013, 15, 104.

    Article  CAS  Google Scholar 

  7. Undeela, S.; Ramchandra, J. P.; Menon, R. S. Tetrahedron Lett. 2014, 55, 5667.

    Article  CAS  Google Scholar 

  8. (a) Gupta, S.; Rastogi, S. N. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 1995, 34, 245. (b) Ziani, N.; Lamara, K.; Sid, A.; Willem, G.; Dassonneville, B.; Demonceau, A. Eur. J. Chem. 2013, 4, 176. (c) El-Zahar, M. I.; Abd El-Karim, S. S.; Anwar, M. M.; Danial, E. M. Pharma Chem. 2010, 2(4), 118.

  9. Boob, S. D.; Solanki, P. R. World J. Pharm. Pharm. Sci. 2015, 4, 1393.

    CAS  Google Scholar 

  10. (a) Rostom, S. A. F.; Badr, M. H.; Abd El Razik, H. A.; Ashour, H. M. A.; Abdel-Wahab, A. E. Arch. Pharm. Chem. Life Sci. 2011, 344, 572. (b) Insuasty, B.; Chamizo, L.; Muñoz, J.; Tigreros, A.; Quiroga, J.; Abonía, R.; Nogueras, M.; Cobo, J. Arch. Pharm. Chem. Life Sci. 2012, 345, 275.

  11. (a) Bajia, B.; Srivastava, Y. K. E-J. Chem. 2007, 4, 187. (b) Rajput, A. P.; Rajput, S. S. Int. J. Pharm. Pharm Sci. 2011, 3, 346. (c) Hassan, S. Y. J. Braz. Chem. Soc. 2011, 22, 1286.

  12. (a) Azarifar, D.; Shaebanzadeh, M. Molecules 2002, 7, 885. (b) Kendre, M. M.; Baseer, M. A. Am. J. Adv. Drug Delivery 2013, 1, 387.

  13. Khalil, O. M.; Refaat, H. M. Orient. J. Chem. 2011, 27, 1581.

    CAS  Google Scholar 

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Authors and Affiliations

  1. A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky St., Irkutsk, 664033, Russia

    Elena Yu. Schmidt, Elena V. Ivanova, Inna V. Tatarinova, Igor A. Ushakov, Nadezhda I. Protsuk & Boris A. Trofimov

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  1. Elena Yu. Schmidt
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  2. Elena V. Ivanova
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  3. Inna V. Tatarinova
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  4. Igor A. Ushakov
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  5. Nadezhda I. Protsuk
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  6. Boris A. Trofimov
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Corresponding author

Correspondence to Boris A. Trofimov.

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Published in Khimiya Geterotsiklicheskikh Soedinenii, 2015, 51(3), 242–245

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Schmidt, E.Y., Ivanova, E.V., Tatarinova, I.V. et al. Base-catalyzed addition of ketones to alkynes as a springboard to cycloalka[c]pyrazoline-2-carbaldehydes. Chem Heterocycl Comp 51, 242–245 (2015). https://doi.org/10.1007/s10593-015-1691-8

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  • DOI: https://doi.org/10.1007/s10593-015-1691-8

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