Unprecedented reaction course of 1-phenyl-2H,6H-imidazo[1,5-c]quinazoline-3,5-dione with 3-M excess of ethylene oxide

Agnieszka Szyszkowska, Karol Hęclik, Sylwia Pawlędzio, Damian Trzybiński, Krzysztof Woźniak, Antonin Klasek, Iwona Zarzyka

Research output: Contribution to journalArticlepeer-review

Abstract

The reaction of 1-phenyl-2H,6H-imidazo[1,5-c]quinazolino-3,5-dione (4) with 3-molar excess ethylene oxide was described. The resulting product was characterized by spectroscopic techniques ( 1 H-, 13 C-NMR, IR, and UV) and by X-ray crystallography. It was expected to produce a product of the subsequent reaction in the hydroxyl groups of the initially formed diol—1-phenyl-2,6-bis(2-hydroxyethyl)imidazo[1,5-c]quinazoline-3,5-dione (7) with ethylene oxide (5). However, crystallographic studies revealed that the proper and only product of the reaction is 3-{2-[1,3-bis(2-hydroxyethyl)-2-oxo-4-phenylimidazolidin-5-yl]phenyl}-1,3-oxazolidin-2-one (8). This product was formed by quinazoline ring opening which occurred in the presence of more than 2-molar excess ethylene oxide. In the work, the exemplary reaction mechanism explaining the formation of the unexpected product was proposed. In order to understand the reasons of quinazoline ring opening, the quantum mechanical modeling was performed. Energy of transition states indicated that the reaction with the third mole of ethylene oxide was controlled by kinetics.

Original languageEnglish
Pages (from-to)1079-1094
Number of pages16
JournalStructural Chemistry
Volume30
Issue number3
DOIs
StatePublished - Jun 15 2019
Externally publishedYes

Funding

The crystallographic study was carried out at the Biological and Chemical Research Centre, University of Warsaw, established within the project co-financed by European Union from the European Regional Development Fund under the Operational Programme Innovative Economy, 2007–2013. Antonin Klasek for the financial support from the internal grant of TBU in Zlin (No. IGA/FT/2017/005), funded from the resources of specific university research.

FundersFunder number
TBU in ZlinIGA/FT/2017/005
European Commission
European Regional Development Fund

    Keywords

    • Crystallographic structure
    • Imidazo[1,5-c]quinazolino-3,5-dione ring
    • Intramolecular substitution
    • Oxirane
    • Quantum mechanical modeling

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