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

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F70883521%3A28110%2F19%3A63523513" target="_blank" >RIV/70883521:28110/19:63523513 - isvavai.cz</a>

Result on the web

<a href="https://link.springer.com/article/10.1007/s11224-018-1247-5" target="_blank" >https://link.springer.com/article/10.1007/s11224-018-1247-5</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1007/s11224-018-1247-5" target="_blank" >10.1007/s11224-018-1247-5</a>

Result language

angličtina

Original language name

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

Original language description

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.

Czech name

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Czech description

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Type

J_imp - Article in a specialist periodical, which is included in the Web of Science database

CEP classification

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OECD FORD branch

10401 - Organic chemistry

Project

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Continuities

S - Specificky vyzkum na vysokych skolach

Publication year

2019

Confidentiality

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Name of the periodical

Structural Chemistry

ISSN

1040-0400

e-ISSN

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Volume of the periodical

30

Issue of the periodical within the volume

3

Country of publishing house

US - UNITED STATES

Number of pages

16

Pages from-to

1079-1094

UT code for WoS article

000467640900042

EID of the result in the Scopus database

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