Molecular rearrangement of pyrazino[2,3-c]quinolin-5(6H)-ones during their reaction with isocyanic acid

Submitting author affiliation:
Tomas Bata University in Zlin, Faculty of Technology, Zlín, Czech Republic

Beilstein Arch. 2021, 202154.

Published 29 Jul 2021

This preprint has not been peer-reviewed. When a peer-reviewed version is available, this information will be updated.


A new tetrahydropyrazino[2,3-c]quinolin-5(6H)-ones were prepared from 3-chloroquinoline-2,4(1H,3H)-diones and ethylene diamine. In their reaction with HNCO, an unprecedented molecular rearrangement produced new types of hydantoin derivatives. All prepared compounds are characterized using their 1H, 13C, and 15N NMR spectra and the results of the X-ray analysis are also presented. A proposed mechanism of rearrangement is discussed in this essay.

Keywords: 3-(3-Acylureido)-2,3-dihydro-1H-indol-2-ones; 4-alkylidene-1´H-spiro[imidazolidine-5,3´-indole]-2,2´-diones; imidazo[1,5-c]quinazoline-3,5-diones; 1H, 13C and 15N NMR; spiro-linked imidazoline-2-thiones; X-ray

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When a peer-reviewed version of this preprint is available, this information will be updated in the information box above. If no peer-reviewed version is available, please cite this preprint using the following information:

Klásek, A.; Lyčka, A.; Křemen, F.; Růžička, A.; Rouchal, M. Beilstein Arch. 2021, 202154. doi:10.3762/bxiv.2021.54.v1

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