Affiliation:
1. Department of Organic and Biomolecular Chemistry Ural Federal University 19 Mira Str. Yekaterinburg 620002 Russia
2. Postovsky Institute of Organic Synthesis Ural Division of the Russian Academy of Sciences 22 S. Kovalevskoy Str. Yekaterinburg 620219 Russia
3. Institute of Chemistry Saint Petersburg State University 7/9 Universitetskaya Nab. Saint Petersburg 198504 Russia
4. Рeoples' Friendship University of Russia (RUDN University) 6 Miklukho-Maklaya Str. Moscow 117198 Russia
Abstract
AbstractThe C−N coupling of 1,2,4‐triazolo[1,5‐a]pyrimidin‐7‐ones with 1‐adamantanol/1‐bromoadamantane leads to 1,2,4‐triazolo[4,3‐a]pyrimidinium‐5‐olates, which are represented as mesomeric betaines (MBs). The formation of MBs involves not only N‐alkylation of heterocyclic framework but also the rearrangement leading to a change in the type of fusion between pyrimidine and 1,2,4‐triazole fragments. The structures of the obtained products were confirmed by the X‐ray analysis and measurements of 13C−13C (JCC) coupling constants in the 1D 13C NMR spectra of selectively 13C‐labeled samples. Treatment of the betaines with lithium bis(trimethylsilyl)amide (LiHMDS) gave anionic carbenes, which were detected by 13C NMR spectroscopy and were trapped by reactions with phenyl isothiocyanate and sulfur. Density functional theory (DFT) and the quantum theory of atoms in molecules (QTAIM) analyses allowed for an insight into the electronic structure of the obtained betaines and N‐heterocyclic carbene derivatives.
Funder
Russian Foundation for Basic Research
Ministry of Science and Higher Education of the Russian Federation
RUDN University
Subject
General Chemistry,Biochemistry,Organic Chemistry
Cited by
3 articles.
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