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

Kód výsledku v 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>

Výsledek na webu

<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>

Jazyk výsledku

angličtina

Název v původním jazyce

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

Popis výsledku v původním jazyce

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.

Název v anglickém jazyce

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

Popis výsledku anglicky

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.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

10403 - Physical chemistry

Projekt

—

Návaznosti

S - Specificky vyzkum na vysokych skolach

Rok uplatnění

2017

Kód důvěrnosti údajů

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

Název periodika

Journal of Molecular Structure

ISSN

0022-2860

e-ISSN

—

Svazek periodika

1127

Číslo periodika v rámci svazku

Neuveden

Stát vydavatele periodika

NL - Nizozemsko

Počet stran výsledku

8

Strana od-do

708-715

Kód UT WoS článku

000385901800081

EID výsledku v databázi Scopus

2-s2.0-84983454279