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Article

Molecular Rearrangement of Pyrazino[2,3-c]quinolin-5(6H)-ones during Their Reaction with Isocyanic Acid

1
Department of Chemistry, Faculty of Technology, Tomas Bata University in Zlín, Vavrečkova 5669, 760 01 Zlín, Czech Republic
2
Department of Chemistry, Faculty of Science, University of Hradec Králové, Rokitanského 62, 530 03 Hradec Králové, Czech Republic
3
Department of General and Inorganic Chemistry, Faculty of Chemical Technology, University of Pardubice, Studentská 573, 532 10 Pardubice, Czech Republic
*
Author to whom correspondence should be addressed.
Academic Editor: Toshiyuki Kaji
Int. J. Mol. Sci. 2022, 23(10), 5481; https://doi.org/10.3390/ijms23105481 (registering DOI)
Received: 13 April 2022 / Revised: 5 May 2022 / Accepted: 12 May 2022 / Published: 13 May 2022
(This article belongs to the Special Issue Heterocyclic Compounds: Advanced Syntheses and Applications)
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 were characterized on the basis of their 1H, 13C, and 15N NMR and ESI mass spectra and some were authenticated by X-ray analysis of single crystalline material. A proposed mechanism for rearrangement is discussed in this essay. The CDK and ABL inhibition activity as well as in vitro cytotoxicity of the prepared compounds was also tested. View Full-Text
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; scXRD; biological activity 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; scXRD; biological activity
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MDPI and ACS Style

Klásek, A.; Lyčka, A.; Křemen, F.; Růžička, A.; Rouchal, M. Molecular Rearrangement of Pyrazino[2,3-c]quinolin-5(6H)-ones during Their Reaction with Isocyanic Acid. Int. J. Mol. Sci. 2022, 23, 5481. https://doi.org/10.3390/ijms23105481

AMA Style

Klásek A, Lyčka A, Křemen F, Růžička A, Rouchal M. Molecular Rearrangement of Pyrazino[2,3-c]quinolin-5(6H)-ones during Their Reaction with Isocyanic Acid. International Journal of Molecular Sciences. 2022; 23(10):5481. https://doi.org/10.3390/ijms23105481

Chicago/Turabian Style

Klásek, Antonín, Antonín Lyčka, Filip Křemen, Aleš Růžička, and Michal Rouchal. 2022. "Molecular Rearrangement of Pyrazino[2,3-c]quinolin-5(6H)-ones during Their Reaction with Isocyanic Acid" International Journal of Molecular Sciences 23, no. 10: 5481. https://doi.org/10.3390/ijms23105481

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