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Fluorescent triazolyl spirooxazolidines: Synthesis and NMR stereochemical studies
KTH, School of Industrial Engineering and Management (ITM), Materials Science and Engineering. Department of Multilayer Materials, Institute of Metallurgy and Materials Science, Polish Academy of Sciences, Reymonta 25 st., Kraków, 30-059, Poland.
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2019 (English)In: Journal of Molecular Structure, ISSN 0022-2860, E-ISSN 1872-8014, Vol. 1183, p. 157-167Article in journal (Refereed) Published
Abstract [en]

Carbon-heteoratom chemistry is a method of choice for rapid construction of complex molecules. In the recent decade, its various applications flourished thanks to the click chemistry approach. Herein, we use a combination of C-X bond formation reactions to complete the synthesis of 1,2,3-triazolyl spirooxazolidines, bearing the fluorenylmethoxycarbonyl (fmoc) substituent. Thanks to the application of 2D-NMR spectroscopic methods and a multilevel computational approach, including a medicinal chemistry – inspired conformational search, PM7 semiempirical and DFT-based geometry optimization finalized with DFT-GIAO NMR shielding constant calculation, we were able to investigate the conformational space and assign cis/trans configuration in complex NMR spectra. For the obtained fmoc derivatives we recorded UV-VIS absorption and emission spectra. The obtained compounds contain pharmacophoric groups characteristic for endocannabinoid system modulators- CB1 receptor ligands or FAAH inhibitors.

Place, publisher, year, edition, pages
Elsevier, 2019. Vol. 1183, p. 157-167
Keywords [en]
NMR, Oxazolidine, Spirooxazolidine, Stereochemistry, Triazole
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:kth:diva-244176DOI: 10.1016/j.molstruc.2019.01.052ISI: 000459865900018Scopus ID: 2-s2.0-85060865198OAI: oai:DiVA.org:kth-244176DiVA, id: diva2:1289469
Note

QC 20190218

Available from: 2019-02-18 Created: 2019-02-18 Last updated: 2019-03-19Bibliographically approved

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Trybula, Marcela

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