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

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dc.title Synthesis, spectroscopic characterization and DFT calculations of monohydroxyalkylated derivatives of 1-phenyl-2H,6H-imidazo[1,5-c]quinazoline-3,5-dione en
dc.contributor.author Szyszkowska, Agnieszka
dc.contributor.author Hęclik, Karol
dc.contributor.author Trzybiński, Damian
dc.contributor.author Woźniak, Krzysztof
dc.contributor.author Klásek, Antonín
dc.contributor.author Zarzyka, Iwona
dc.relation.ispartof Journal of Molecular Structure
dc.identifier.issn 0022-2860 OCLC, Ulrich, Sherpa/RoMEO, JCR
dc.date.issued 2017
utb.relation.volume 1127
dc.citation.spage 708
dc.citation.epage 715
dc.type article
dc.language.iso en
dc.publisher Elsevier
dc.identifier.doi 10.1016/j.molstruc.2016.08.025
dc.relation.uri https://www.sciencedirect.com/science/article/pii/S0022286016308559
dc.subject 1-phenyl-2H,6H-imidazo[1,5-c]quinazoline-3,5-dione en
dc.subject Chemoselectivity en
dc.subject Oxiranes en
dc.subject Quantum mechanical calculations en
dc.subject Synthesis en
dc.description.abstract 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 (1H, 13C 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–LUMO 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. © 2016 Elsevier B.V. en
utb.faculty Faculty of Technology
dc.identifier.uri http://hdl.handle.net/10563/1006626
utb.identifier.obdid 43877126
utb.identifier.scopus 2-s2.0-84983454279
utb.identifier.wok 000385901800081
utb.identifier.coden JMOSB
utb.source j-scopus
dc.date.accessioned 2016-10-25T12:38:00Z
dc.date.available 2016-10-25T12:38:00Z
dc.description.sponsorship Interdisciplinary Centre for Mathematical and Computational Modelling in Warsaw [G49-12]; TBU in Zlin [IGA/FT/2016/004]
utb.contributor.internalauthor Klásek, Antonín
utb.fulltext.affiliation Agnieszka Szyszkowska a , Karol Hęclik b , Damian Trzybi n, Krzysztof Woźniak c , Antonin Klasek d , Iwona Zarzyka a, * a Department of Organic Chemistry, Faculty of Chemistry, Rzeszów University of Technology, Powstańców Warszawy 6, 35-959 Rzeszow, Poland b Department of Biotechnology and Bioinformatics, Faculty of Chemistry, Rzeszów University of Technology, Powstańców Warszawy 6, 35-959 Rzeszow, Poland c Department of Chemistry, Biological and Chemical Research Centre, University of Warsaw, Żwirki i Wigury 101, 02-089, Warsaw, Poland d Department of Chemistry, Faculty of Technology, Tomas Bata University in Zlin, CZ-762 72 Zlin, Czech Republic * Corresponding author. E-mail address: izarzyka@prz.edu.pl (I. Zarzyka).
utb.fulltext.dates Received 6 April 2016 Received in revised form 18 July 2016 Accepted 10 August 2016 Available online 13 August 2016
utb.fulltext.sponsorship The authors would like to thank Interdisciplinary Centre for Mathematical and Computational Modelling in Warsaw for providing computer facilities for possibility of performing of the quantum-mechanical calculations under grant G49-12. Antonin Klasek thanks for the financial support from the internal grant of TBU in Zlín (No. IGA/FT/2016/004), funded from the resources of specific university research.
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