Beilstein Talk on achieving molecular complexity via metal-free domino reactions

Beilstein Talks


The Beilstein Talks are an established addition to the Beilstein-Institut’s projects supporting communication and information in science. These online talks are free to attend; a simple registration is all that is required.

Achieving molecular complexity via metal-free domino reactions 


Svetlana B. Tsogoeva
/ Friedrich-Alexander-Universität Erlangen-Nürnberg
January 18
, 2023, 3 - 4 pm CET

Online live talk


Go to the free registration for the online live talk!

A domino process is a powerful tool to economically and sustainably build up complex molecular architectures which drastically reduces the number of work-up and purification steps. Recently, we developed new metal-free multi-step domino reactions and one-pot processes for the waste-reducing and cost-effective preparation of versatile frameworks, which otherwise are difficult to access via traditional methods. The developed new methods engage simple and readily available compounds in a wide range of domino reactions to construct e.g., azabicycles, quinazolines, quinazoline-thiohydantoins, 2,6-dicyanoanilines, o‐terphenyls and hexaarylbenzenes of interest for medicinal chemistry and materials science. Very recently, we disclosed a versatile autocatalytic transamination metathesis reaction, which is a multi-step domino process. This novel methodology gives rapid and atom-economical access to N-substituted 1,4-dihydropyridines, which are privileged structures in bioactive compounds and pharmaceuticals.

The in vitro tests against multidrug‐resistant P. falciparum strains (Dd2 and K1), human cytomegalovirus (HCMV), and multidrug-resistant P glycoprotein-overexpressing CEM/ADR5000 leukemia cells revealed the selected domino products and some corresponding artemisinin-containing hybrid compounds as highly active agents, outperforming the clinical reference drugs. These recent results will be discussed in the talk.

 

Selected references

[1] F. E. Held, A. A. Guryev, T. Fröhlich, F. Hampel, A. Kahnt, C. Hutterer, M. Steingruber, A. Nesterov-Mueller, M. Marschall, S. B. Tsogoeva, Nature Commun., 2017, 8:15071.

[2] A. Çapcı, M. M. Lorion, H. Wang, N. Simon, M. Leidenberger, M. C. Borges Silva, D. R. M. Moreira, O. Friedrich, B. Kappes, J. Wang, L. Ackermann, S. B. Tsogoeva, Angew. Chem. Int. Ed., 2019, 58:13066.

[3] B. W. Grau, M. Dill, F. Hampel, A. Kahnt, N. Jux, S. B. Tsogoeva. Angew. Chem. Int. Ed., 2021, 60:22307.

[4] V. Klein, F. Schuster, S. B. Tsogoeva. Preprint: ChemRxiv. 2022, https://doi.org/10.26434/chemrxiv-2022-m6k1v.

11 Jan 2023

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