Skip to main content
SpringerLink
Log in

On the question of selective protocol for the preparation of juglone via (4+2) cycloaddition involving 3-hydroxypyridazine: DFT mechanistic study

  • SHORT COMMUNICATION
  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

The possibility of preparation of juglone via Diels–Alder reaction of 3-hydroxypyridazine and 2-nitroquinone was analyzed on the basis of DFT computational study. It was found that key stage of the proposed transformation is head-to-head, polar cycloaddition process, which is realized without formation of zwitterionic intermediate. Further transformations of the intermediate exhibit nature of pseudocyclic reactions with nonconcerted reorganization of the electron density.

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Scheme 1
Figure 1.
Figure 2.
Figure 3.

Similar content being viewed by others

References

  1. (a) Domingo, L. R.; Ríos-Gutiérrez, M.; Chamorro, E.; Pérez, P. ChemistrySelect 2016, 1, 6026. (b) Jasiński, R. Comput. Theor. Chem. 2018, 1125, 77. (c) Jasiński, R.; Kula, K.; Kącka, A.; Mirosław, B. Monatsh. Chem. 2017, 148, 909. (d) Mirosław, B.; Babyuk, D.; Łapczuk-Krygier, A.; Kącka-Zych, A.; Demchuk, O. M.; Jasiński, R. Monatsh. Chem. 2018, 149, 1877.

  2. (a) Lapinski, L.; Fulara, J.; Czerminski, R.; Nowak, M. J. Spectrochim. Acta, Part A 1990, 46, 1087. (b) Tavares, F. X.; Boucheron, J. A.; Dickerson, S. H.; Griffin, R. J.; Preugschat, F.; Thomson, S. A.; Wang, T. Y.; Zhou, H.-Q. J. Med. Chem. 2004, 47, 4716.

  3. (a) Chen, Yu.; Ying, W.; Harmata, M. Tetrahedron Lett. 2011, 52, 480. (b) Polgatti, V.; Valderrama, J. A.; Tapia, R. Synth. Commun. 1990, 20, 1085.

  4. (a) Jasiński, R. React. Kinet., Mech. Catal. 2016, 119, 49. (b) Houk, K. N.; Liu, F.; Yang, Z.; Seeman, J. I. Angew. Chem., Int. Ed. 2021, 60, 12660.

  5. (a) Jasiński, R. J. Mol. Graphics Modell. 2017, 75, 55. (b) Jasiński, R. Comput. Theor. Chem. 2014, 1046, 93. (c) Jasiński, R. J. Fluorine Chem. 2018, 206, 1. (d) Ernd, M.; Heuschmann, M.; Zipse, H. Helv. Chim. Acta 2005, 88, 1491.

  6. Jasiński, R. Symmetry 2021, 13, 1911.

    Google Scholar 

  7. Kula, K.; Dobosz, J.; Jasiński, R.; Kącka-Zych, A.; Łapczuk-Krygier, A.; Mirosław, B.; Demchuk, O. M. J. Mol. Struct. 2020, 1203, 127473.

    Article  CAS  Google Scholar 

  8. Kącka-Zych, A.; Jasiński, R. New J. Chem. 2021, 45, 9491.

    Article  Google Scholar 

  9. Jasiński, R.; Mirosław, B.; Demchuk, O. M.; Babyuk, D.; Łapczuk-Krygier, A. J. Mol. Struct. 2016, 1108, 689.

    Article  Google Scholar 

  10. (a) Domingo, L. R. RSC Adv. 2014, 4, 32415. (b) Domingo, L. R.; Ríos-Gutiérrez, M. Sci. Rad. 2023, 2, 1.

  11. Domingo, L. R. Molecules 2016, 21, 1319.

    Article  PubMed  PubMed Central  Google Scholar 

  12. Jasiński, R. RSC Adv. 2015, 5, 50070.

    Article  Google Scholar 

  13. Woliński, P.; Kącka-Zych, A.; Demchuk, O. M.; Łapczuk-Krygier, A.; Mirosław, B.; Jasiński, R. J. Clean. Product. 2020, 275, 122086.

    Article  Google Scholar 

  14. Kącka, A.; Jasiński, R. Heteroat. Chem. 2016, 27, 279.

    Article  Google Scholar 

  15. Domingo, L. R.; Sáez, J. A. Org. Biomol. Chem. 2009, 7, 3576.

    Article  CAS  PubMed  Google Scholar 

  16. Chai J.-D.; Head-Gordon, M. Phys. Chem. Chem. Phys. 2008, 10, 6615.

    Article  CAS  PubMed  Google Scholar 

  17. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A., Jr.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, J. M.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, Ö.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian 09, Revision D.01; Gaussian, Inc.: Wallingford, 2013.

  18. Scalmani, G.; Frisch, M. J. J. Chem. Phys. 2010, 132, 114110.

    Article  PubMed  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Organic Chemistry and Technology, Cracow University of Technology, 24 Warszawska St., 31-155, Cracow, Poland

    Radomir Jasiński

Authors
  1. Radomir Jasiński
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Radomir Jasiński.

Additional information

Published in Khimiya Geterotsiklicheskikh Soedinenii, 2023, 59(3), 179–182

Rights and permissions

Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Jasiński, R. On the question of selective protocol for the preparation of juglone via (4+2) cycloaddition involving 3-hydroxypyridazine: DFT mechanistic study. Chem Heterocycl Comp 59, 179–182 (2023). https://doi.org/10.1007/s10593-023-03180-4

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-023-03180-4

Keywords

Search

Navigation