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

Antonín Klásek; Antonín Lyčka; Filip Křemen; Aleš Růžička; Michal Rouchal

doi:10.3762/bxiv.2021.54.v1

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

Antonín Klásek ,
Antonín Lyčka,
Filip Křemen,
Aleš Růžička and
Michal Rouchal

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

Beilstein Arch. 2021, 202154. https://doi.org/10.3762/bxiv.2021.54.v1

Published 29 Jul 2021

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This preprint has not been peer-reviewed.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

Abstract

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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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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aromatic	the word “aromatic”
aromatic aldehyde	the word “aromatic” OR “aldehyde”
+aromatic +aldehyde	both words “aromatic” AND “aldehyde”
+aromatic -aldehyde	the word “aromatic” but NOT “aldehyde”
“aromatic aldehyde”	the exact phrase “aromatic aldehyde”
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Molecular rearrangement of pyrazino[2,3-c]quinolin-5(6H)-ones during their reaction with isocyanic acid

This preprint has not been peer-reviewed.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

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