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Acenaphthenequinone-Based Stabilized Azomethine Ylides in (3+2) Cycloaddition Reactions with 1,5-diarylpent-4-ene-1,3-diones

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Chemistry of Heterocyclic Compounds Aims and scope

A regio- and stereoselective method for the synthesis of spiro[acenaphthylenepyrroli(zi)din]-2-ones containing a 1,3-diketone fragment in their structure in 57–93% yields was developed. The method is based on (3+2) cycloaddition of azomethine ylides generated in situ from acenaphthenequinone and α-amino acids (L-(thia)proline, L-phenylglycine) to (E)-1,5-diarylpent-4-ene-1,3-diones in EtOH at 60–70°C for 4–8 h.

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References

  1. Kumar, R. S.; Antonisamy, P.; Almansour, A. I.; Arumugam, N.; Al-thamili, D. M.; Kumar, R. R.; Kim, H.-R.; Kwon, K.-B. Bioorg. Chem. 2019, 91, 103180.

    Article  CAS  Google Scholar 

  2. Wei, A. C.; Ali, M. A.; Yoon, Y. K.; Ismail, R.; Choon, T. S.; Kumar, R. S. Bioorg. Med. Chem. Lett. 2013, 23, 1383.

    Article  CAS  Google Scholar 

  3. Dandia, A.; Kumari, S.; Soni, P. Eur. Chem. Bull. 2013, 2, 1004.

    CAS  Google Scholar 

  4. Periyasami, G.; Arumugam, N.; Rahaman, M.; Kumar, R. S.; Manikandan, M.; Alfayez, M. A.; Premnath, D.; Aldalbahi, A. RSC Adv. 2018, 8, 16303.

    Article  CAS  Google Scholar 

  5. (a) Döndas, H. A.; de Gracia Retamosa, M.; Sansano, J. M. Synthesis 2017, 2819. (b) Arumugam, N.; Kumar, R. S.; Almansour, A. I.; Perumal, S. Curr. Org. Chem. 2013, 17, 1929. (c) Najera, C.; Sansano, J. M. Pure Appl. Chem. 2019, 91, 575. (d) Izmest'ev, A. N.; Gazieva, G. А.; Kravchenko, A. N. Chem. Heterocycl. Compd. 2020, 56, 255. [Khim. Geterotsikl. Soedin. 2020, 56, 255.] (e) Molteni, G.; Silvani, A. Eur. J. Org. Chem. 2021, 1653. e Singh, R.; Bhardwaj, D.; Saini, M. R. RSC Adv. 2021, 11, 4760. f Korotaev, V. Yu.; Zimnitskiy, N. S.; Barkov, A. Yu.; Kutyashev, I. B.; Sosnovskikh, V. Ya. Chem. Heterocycl. Compd. 2018, 54, 905. [Khim. Geterotsikl. Soedin. 2018, 54, 905.] (h) Xiong, Y.; Han, X.-X.; Lu, Y.; Wang, H.-J.; Zhang, M.; Liu, X.-W. Tetrahedron 2021, 87, 132112. g Ling, Y.; Huang, Y.; Li, X. Chem. Heterocycl. Compd. 2021, 57, 181. [Khim. Geterotsikl. Soedin. 2021, 57, 181.] (j) Chithiraikumar, C.; Ponmuthu, K. V.; Harikrishnan, M.; Malini, N.; Sepperumal, M.; Siva, A. Res. Chem. Intermed. 2021, 47, 895. h Pavlovska, T. L.; Lipson, V. V.; Shishkina, S. V.; Musatov, V. I.; Borisov, A. V.; Mazepa, A. V. Chem. Heterocycl. Compd. 2019, 55, 679. [Khim. Geterotsikl. Soedin. 2019, 55, 679.] (l) Filatov, A. S.; Knyazev, N. A.; Molchanov, A. P.; Panikorovsky, T. L.; Kostikov, R. R.; Larina, A. G.; Boitsov, V. M.; Stepakov, A. V. J. Org. Chem. 2017, 82, 959. i Barkov, A. Yu.; Zimnitskiy, N. S.; Kutyashev, I. B.; Korotaev, V. Yu.; Sosnovskikh, V. Ya. Chem. Heterocycl. Compd. 2017, 53, 1315. [Khim. Geterotsikl. Soedin. 2017, 53, 1315.] (n) Klochkova, I. N.; Shchekina, M. P.; Anis'kov, A. A. Chem. Heterocycl. Compd. 2014, 50, 479. [Khim. Geterotsikl. Soedin. 2014, 527.]

  6. (a) Kumar, R. S.; Almansour, A. I.; Arumugam, N.; Periyasami, G.; Athimoolam, S.; Kumar, R. R.; Asad, M.; Asiri, A. M. Tetrahedron Lett. 2018, 59, 3336. (b) Yavari, I.; Baoosi, L.; Halvagar, M. R. Synlett 2018, 635. (c) Kutyashev, I. B.; Sannikov M. S.; Kochnev, I. A.; Barkov, A. Yu.; Zimnitskiy, N. S.; Korotaev, V. Yu.; Sosnovskikh, V. Ya. SynOpen 2021, 5, 1. (d) Maurya, R. A.; Nayak, R.; Reddy, C. N.; Kapure, J. S.; Nanubolu, J. B.; Singarapu, K. K.; Ajitha, M.; Kamal, A. RSC Adv. 2014, 4, 32303. (e) Boudriga, S.; Haddad, S.; Murugaiyah, V.; Askri, M.; Knorr, M.; Strohmann, C.; Golz, C. Molecules 2020, 25, 1963. (f) Shahrestani, N.; Khosravi, H.; Jadidi, K.; Notash, B.; Naderi, S. Org. Biomol. Chem. 2019, 17, 7013. (g) Purushothaman, S.; Prasanna, R.; Raghunathan, R. Tetrahedron 2013, 69, 9742. (h) Shi, C.; Zhou, J. Heterocycles 2015, 91, 1972. (i) Rouatbi, F.; Askri, M.; Nana, F.; Kirsch, G.; Sriram, D.; Yogeeswari, P. Tetrahedron Lett. 2016, 57, 163. (j) Thimmarayaperumal, S.; Shanmugam, S. New J. Chem. 2018, 42, 4061. (k) Dandia, A.; Parewa, V.; Kumari, S.; Bansal, S.; Sharma, A. Green Chem. 2016, 18, 2488. (l) Sivakumar, S.; Kumar, R. R.; Ali, M. A.; Choon, T. S. Eur. J. Med. Chem. 2013, 65, 240. (m) Sumesh, R. V.; Shylaja, A.; Kumar, R. R.; Almansour, A. I.; Kumar, R. S. Tetrahedron Lett. 2018, 59, 4086.

  7. (a) Arrieta, A.; Beyer, L.; Kleinpeter, E.; Lehmann, J.; Dargatz, M. J. Prakt. Chem. 1992, 334, 696. (b) Jang, Y.-J.; Chen, Y.-S.; Lee, C.-J.; Chen, C.-H.; Lin, W. Synthesis 2015, 95. (c) Pinto, J.; Silva, V. L. M.; Silva, A. M. G.; Silva, A. M. S. Molecules 2015, 20, 11418. (d) 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. (e) Thomas, A. R.; Shuler, W. G.; Smith, E. A.; Carlisle, S. S.; Knick, S. L.; Puciaty, A. J.; Metz, C. R.; VanDerveer, D. G.; McMillen, C. D.; Pennington, W. T.; Beam, C. F. J. Chem. Crystallogr. 2013, 43, 629.

  8. (a) Zimnitskiy, N. S.; Barkov, A. Yu.; Ulitko, M. V.; Kutyashev, I. B.; Korotaev, V. Yu.; Sosnovskikh, V. Ya. New J. Chem. 2020, 44, 16185. (b) Korotaev, V. Yu.; Zimnitskiy, N. S.; Denikaev, A. D.; Barkov, A. Yu.; Kutyashev, I. B.; Sosnovskikh, V. Ya. Chem. Heterocycl. Compd. 2021, 57, 81. [Khim. Geterotsikl. Soedin. 2021, 57, 81.]

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

    Article  CAS  Google Scholar 

  10. (a) Sheldrick, G. M. Acta Crystallogr., Sect. A: Found. Crystallogr. 2008, A64, 112. (b) Dolomanov, O. V.; Bourhis, L. J.; Gildea, R. J.; Howard, J. A. K.; Puschmann, H. J. Appl. Crystallogr. 2009, 42, 339.

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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 Lenina Ave, Yekaterinburg, 620000, Russia

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

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

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2021, 57(7/8), 743–750

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Zimnitskiy, N.S., Barkov, A.Y., Kutyashev, I.B. et al. Acenaphthenequinone-Based Stabilized Azomethine Ylides in (3+2) Cycloaddition Reactions with 1,5-diarylpent-4-ene-1,3-diones. Chem Heterocycl Comp 57, 743–750 (2021). https://doi.org/10.1007/s10593-021-02978-4

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