Synthesis, spectroscopic characterization and DFT calculations of monohydroxyalkylated derivatives of 1-phenyl-2H,6H-imidazo[1,5-c]quinazoline-3,5-dione

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F70883521%3A28110%2F17%3A63517127" target="_blank" >RIV/70883521:28110/17:63517127 - isvavai.cz</a>

Result on the web

<a href="http://www.sciencedirect.com/science/article/pii/S0022286016308559" target="_blank" >http://www.sciencedirect.com/science/article/pii/S0022286016308559</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1016/j.molstruc.2016.08.025" target="_blank" >10.1016/j.molstruc.2016.08.025</a>

Result language

angličtina

Original language name

Synthesis, spectroscopic characterization and DFT calculations of monohydroxyalkylated derivatives of 1-phenyl-2H,6H-imidazo[1,5-c]quinazoline-3,5-dione

Original language description

Synthesis of new derivatives with an imidazo[1,5-c]quinazoline-3,5-dione ring has been presented. Two new alcohols with the imidazo[1,5-c]quinazoline-3,5-dione ring were obtained and characterized by spectral (H-1, C-13 NMR, IR and UV) and crystallography methods. A reaction chemoselectivity has been observed, with, a formation of monohydroxyalkyl derivatives of 1-phenyl-2H,6H-imidazo[1,5-c]quinazoline-3,5-dione substituted at the 2. nitrogen atom. The absence of derivatives substituted at the 6. nitrogen atom was proven experimentally. The synthesis with chemoselectivity over 99% without control of the substituent effect happens very rarely. The HOMO LLIMO mappings are reported which reveals the different charge transfer possibilities within the molecule of 1-phenyl-2H,6H-imidazo[1,5-c]quinazoline-3,5-dione in the region of the 2. and the 6. nitrogen atoms. Quantum-mechanical DFT calculations proved to be very useful to explain the reason of selectivity reaction of 1-phenyl-2H,6H-imidazo[1,5-c] quinazoline-3,5-dione with oxiranes.

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

10403 - Physical chemistry

Project

—

Continuities

S - Specificky vyzkum na vysokych skolach

Publication year

2017

Confidentiality

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

Name of the periodical

Journal of Molecular Structure

ISSN

0022-2860

e-ISSN

—

Volume of the periodical

1127

Issue of the periodical within the volume

Neuveden

Country of publishing house

NL - THE KINGDOM OF THE NETHERLANDS

Number of pages

8

Pages from-to

708-715

UT code for WoS article

000385901800081

EID of the result in the Scopus database

2-s2.0-84983454279