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(3+2) Cycloaddition of N-benzylazomethine methylide with 4-arylidene-1H-imidazol-5(4H)-ones

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Chemistry of Heterocyclic Compounds Aims and scope

4-Arylidene-1H-imidazol-5(4H)-ones react with N-benzylazomethine methylide under trifluoroacetic acid catalysis to form 9-aryl-1,3,7- triazaspiro[4.4]non-1-en-4-ones in 66–95% yields as one diastereomer in each case.

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References

  1. Undheim, K. Synthesis2014, 1957.

  2. (a) Zheng, Y.; Tice, C. M.; Singh, S. B. Bioorg. Med. Chem. Lett.2014, 24, 3673. (b) Burkhard, J.; Wagner, B.; Fischer, H.; Schuler, F.; Müller, K.; Carreira, E. Angew. Chem., Int. Ed.2010, 49, 3524.

  3. Kotha, S.; Panguluri, N. R.; Ali, R. Eur. J. Org. Chem. 2017, 5316.

  4. (a) Potin, D.; Launay, M.; Monatlik, F.; Malabre, P.; Fabreguettes, M.; Fouquet, A.; Maillet, M.; Nicolai, E.; Dorgeret, L.; Chevallier, F.; Besse, D.; Dufort, M.; Caussade, F.; Ahmad, S. Z.; Stetsko, D. K.; Skala, S.; Davis, P. M.; Balimane, P.; Patel, K.; Yang, Z.; Marathe, P.; Postelneck, J.; Townsend, R. M.; Goldfarb, V.; Sheriff, S.; Einspahr, H.; Kish, K.; Malley, M. F.; DiMarco, J. D.; Gougoutas, J. Z.; Kadiyala, P.; Cheney, D. L.; Tejwani, R. W.; Murphy, D. K.; Mcintyre, K.W.; Yang, X.; Chao, S.; Leith, L.; Xiao, Z.; Mathur, A.; Chen, B.-C.; Wu, D.-R.; Traeger, S. C.; McKinnon, M.; Barrish, J. C.; Robl, J. A.; Iwanowicz, E. J.; Suchard, S. J.; Dhar, T. G. M. J. Med. Chem.2006, 49, 6946. (b) Watterson, S. H.; Xiao, Z.; Dodd, D. S.; Tortolani, D. R.; Vaccaro, W.; Potin, D.; Launay, M.; Stetsko, D. K.; Skala, S.; Davis, P. M.; Lee, D.; Yang, X.; McIntyre, K. W.; Balimane, P.; Patel, K.; Yang, Z.; Marathe, P.; Kadiyala, P.; Tebben, A. J.; Sheriff, S.; Chang, C. Y.; Ziemba, T.; Zhang, H.; Chen, B.-C.; DelMonte, A. J.; Aranibar, N.; McKinnon, M.; Barrish, J. C.; Suchard, S. J.; Dhar, T. G. M. J. Med. Chem.2010, 53, 3814. (c) DelMonte, A. J.; Fan, Y.; Girard, K. P.; Jones, G. S.; Waltermire, R. E.; Rosso, V.; Wang, X. Org. Process Res. Dev. 2011, 15, 64.

  5. Lebwohl, M.; Tyring, S. K.; Hamilton, T. K.; Toth, D.; Glazer, S.; Tawfik, N. H.; Walicke, P.; Dummer, W.; Wang, X.; Garovoy, M. R.; Pariser, D. N. Engl. J. Med.2003, 349, 2004.

    Article  CAS  Google Scholar 

  6. (a) He, J.; Ouyang, G.; Yuan, Z.; Tong, R.; Shi, J.; Ouyang, L. Molecules2013, 18, 5142. (b) Ivanenkov, Y. A.; Vasilevski, S. V.; Beloglazkina, E. K.; Kukushkin, M. E.; Machulkin, A. E.; Veselov, M. S.; Chufarova, N. V.; Chernyagina, E. S.; Vanzcool, A. S.; Zyk, N. V.; Skvortsov, D. A.; Khutornenko, A. A.; Rusanov, A. L.; Tonevitsky, A. G.; Dontsova, O. A.; Majouga, A. G. Bioorg. Med. Chem. Lett.2015, 25, 404. (c) 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.]

  7. (a) Ivashkin, P. E.; Yampolsky, I. V.; Lukyanov, K. A. Russ. J. Bioorg. Chem.2009, 35, 652. [Bioorg. Khim.2009, 35, 726.] (b) Baranov, M. S.; Solntsev, K. M.; Lukyanov, K. A.; Yampolsky, I. V. Chem. Commun. 2013, 49, 5778. b Povarova, N. V.; Zaitseva, S. O.; Baleeva, N. S.; Smirnov, A. Yu.; Myasnyanko, I. N.; Zagudaylova, M. B.; Bozhanova, N. G.; Gorbachev, D. A.; Malyshevskaya, K. K.; Gavrikov, A. S.; Mishin, A. S.; Baranov, M. S. Chem.–Eur. J.2019, 25, 9592.

  8. (a) Terao, Y.; Imai, N.; Achiwa, K. Chem. Pharm. Bull.1987, 35, 1596. (b) Hosomi, A.; Sakata, Y.; Sakurai, H. Chem. Lett. 1984, 1117.

  9. Coldham, I.; Hufton, R. Chem. Rev. 2005, 105, 2765.

    Article  CAS  Google Scholar 

  10. Dolomanov, O. V.; Bourhis, L. J.; Gildea, R. J.; Howard, J. A. K.; Puschmann, H. J. Appl. Crystallogr.2009, 42, 339.

    Article  CAS  Google Scholar 

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

  12. Sheldrick, G. M. Acta Crystallogr., Sect. C: Struct. Chem.2015, C71, 3.

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Authors and Affiliations

  1. Shemyakin-Ovchinnikov Institute of Bioorganic Chemistry, Russian Academy of Sciences, 16/10 Miklukho-Maklaya St, Moscow, 117997, Russia

    Andrei V. Kuleshov, Mikhail S. Baranov & Andrey А. Mikhaylov

  2. Moscow M. V. Lomonosov State University, 1, Build. 3 Leninskie Gory, Moscow, 119991, Russia

    Andrei V. Kuleshov

  3. Engelhardt Institute of Molecular Biology, Russian Academy of Sciences, 32 Vavilova St, Moscow, 119991, Russia

    Pavel N. Solyev

  4. A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilova St, Moscow, 119991, Russia

    Alexander D. Volodin & Аlexander А. Korlyukov

Authors
  1. Andrei V. Kuleshov
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  2. Pavel N. Solyev
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  3. Alexander D. Volodin
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  4. Аlexander А. Korlyukov
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  5. Mikhail S. Baranov
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  6. Andrey А. Mikhaylov
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Correspondence to Andrey А. Mikhaylov.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2020, 56(1), 108–111

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Kuleshov, A.V., Solyev, P.N., Volodin, A.D. et al. (3+2) Cycloaddition of N-benzylazomethine methylide with 4-arylidene-1H-imidazol-5(4H)-ones. Chem Heterocycl Comp 56, 108–111 (2020). https://doi.org/10.1007/s10593-020-02630-7

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  • DOI: https://doi.org/10.1007/s10593-020-02630-7

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