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

  1. Antonín KlásekORCID Logo,
  2. Antonín LyčkaORCID Logo,
  3. Filip Křemen,
  4. Aleš Růžička and
  5. Michal RouchalORCID Logo

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

  • Preprint

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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