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

Szyszkowska, A.; Hęclik, Karol; Trzybiński, Damian; Woźniak, Krzysztof; Klásek, Antonı́n; Zarzyka, Iwona

doi:10.1016/j.molstruc.2016.08.025

Cited by 6 publications

(6 citation statements)

References 25 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Signals in the range of 115-140 ppm originated from the carbon atoms of the phenyl ring and imidazoquinazoline ring. Their positions were a bit different from the corresponding peaks found in the 13 C-NMR spectra of alcohol (6) and diol (7) with imidazoquinazoline ring [4,5] (Fig. 8S).…”

Section: S-7s)mentioning

confidence: 61%

“…The reactions were catalyzed with triethylamine (TEA) and maintained at 70-80°C. An alcohol (6) and diol (7) with imidazoquinazoline ring were obtained with an equimolar amount of EO or 2-molar excess of EO as described in BIntroduction^ [4,5]. It was expected to produce etherols (9)(10)(11) with the imidazoquinazoline ring in the reaction of (4) with 3-molarexcess of EO, under conditions analogous to the synthesis of (6) and (7).…”

Section: Resultsmentioning

confidence: 99%

“…In the first step, the molecule (4) attacks the EO molecule (5) by the nitrogen atom no. 2 and 1-phenyl-2-(2-hydroxyethyl)-6H-imidazo[1,5-c]quinazoline-3,5-dione (6) is formed [4].…”

Section: Quantum Mechanical Modeling Of 3-{2-mentioning

confidence: 99%

“…The compound (4) could be reacted with ethylene oxide (EO, 5), and then, alcohol (6) [4] and diol (7) [5] with the imidazoquinazoline rings were successively produced according to the scheme shown in Fig. 2.…”

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

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

et al. 2019

Self Cite

View full text Add to dashboard Cite

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(2hydroxyethyl)-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.

show abstract

Section: S-7s)mentioning

confidence: 61%

Section: Resultsmentioning

confidence: 99%

“…In the first step, the molecule (4) attacks the EO molecule (5) by the nitrogen atom no. 2 and 1-phenyl-2-(2-hydroxyethyl)-6H-imidazo[1,5-c]quinazoline-3,5-dione (6) is formed [4].…”

Section: Quantum Mechanical Modeling Of 3-{2-mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

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

et al. 2019

Self Cite

View full text Add to dashboard Cite

show abstract

“…The reasons for the reaction chemoselectivity during the obtaining of monosubstituted derivatives of PIQ were explained in detail earlier in paper [24]. …”

Section: Resultsmentioning

confidence: 99%

Esters with imidazo [1,5-c] quinazoline-3,5-dione ring spectral characterization and quantum-mechanical modeling

et al. 2017

View full text Add to dashboard Cite

1-phenyl-2H,6H-imidazo[1,5-c]quinazoline-3,5-dione reacts with ethyl bromoacetate under mild conditions to give 2-(ethoxycarbonylmethyl)-1-phenyl-6H-imidazo[1,5-c]quinazoline-3,5-dione (MEPIQ) and next 2,6-bis(ethoxycarbonylmethyl)-1-phenylimidazo[1,5-c]quinazoline-3,5-dione (BEPIQ). The products were isolated at high yield and identified on the basis of IR, 1H- and 13C-NMR, UV spectroscopy, and X-ray crystallography. Diester (BEPIQ) can be presented by 16 possible pair of enantiomers. Only one pair of them is the most stable and crystallizes which is shown crystallographic research. Based on quantum-mechanical modeling, with the use of DFT method, which conformers of mono- and diester and why they were formed was explained. It was calculated that 99.93% of the monoester (MEPIQ) is formed at position No. 2 and one pair of the monoester conformers, from six possible, has the largest share (51.63%). These results afforded to limit the number of diester conformers to eight. Unfortunately, the quantum-mechanical calculations performed that their shares are similar. Further quantum-mechanical modeling showed that conformers are able to undergo mutual transformations. As a result only one pair of diester conformers forms crystals. These conformers have substituents in trans position and these substituents are located parallel to imidazoquinazoline ring. This allows for the denser packing of the molecules in the unit cell.Electronic supplementary materialThe online version of this article (doi:10.1007/s00894-017-3284-1) contains supplementary material, which is available to authorized users.

show abstract

Quinazolines annelated at the N(3)–C(4) bond: Synthesis and biological activity

Nosova,

Lipunova,

Permyakova

et al. 2024

European Journal of Medicinal Chemistry

View full text Add to dashboard Cite

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

Cited by 6 publications

References 25 publications

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

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

Esters with imidazo [1,5-c] quinazoline-3,5-dione ring spectral characterization and quantum-mechanical modeling

Quinazolines annelated at the N(3)–C(4) bond: Synthesis and biological activity

Contact Info

Product

Resources

About