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

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dc.abstract.enThe reaction of 1-phenyl-2H,6H-imidazo[1,5-c]quinazolino-3,5-dione (4) with 3-molar excess ethylene oxide was de-cribed. The resulting product was characterized by spectroscopic techniques (1H-, 13C-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.
dc.affiliationUniwersytet Warszawski
dc.contributor.authorKlasek, Antonin
dc.contributor.authorZarzyka, Iwona
dc.contributor.authorSzyszkowska, Agnieszka
dc.contributor.authorHęclik, Karol
dc.contributor.authorTrzybiński, Damian
dc.contributor.authorWoźniak, Krzysztof
dc.contributor.authorPawlędzio, Sylwia
dc.date.accessioned2024-01-26T11:19:46Z
dc.date.available2024-01-26T11:19:46Z
dc.date.copyright2019-01-08
dc.date.issued2019
dc.description.accesstimeAT_PUBLICATION
dc.description.financeNie dotyczy
dc.description.number3
dc.description.versionFINAL_PUBLISHED
dc.description.volume30
dc.identifier.doi10.1007/S11224-018-1247-5
dc.identifier.issn1040-0400
dc.identifier.urihttps://repozytorium.uw.edu.pl//handle/item/124238
dc.identifier.weblinkhttps://link.springer.com/article/10.1007/s11224-018-1247-5
dc.languageeng
dc.pbn.affiliationchemical sciences
dc.relation.ispartofStructural Chemistry
dc.relation.pages1079-1094
dc.rightsOther
dc.sciencecloudnosend
dc.subject.enImidazo[1,5-c]quinazolino-3,5-dione ring . Oxirane . Intramolecular substitution . Crystallographic structure . Quantum mechanical modeling
dc.titleUnprecedented reaction course of 1-phenyl-2H,6H-imidazo[1,5-c]quinazoline-3,5-dione with an excess of ethylene oxide
dc.typeJournalArticle
dspace.entity.typePublication