Biomedical Chemistry: Research and Methods, 2018, 1(3), e00016
The 40th Anniversary of the Institute of Physiologically Active Compounds of the Russian Academy of Sciences

Carbamoylimines of Methyltrifluoropyruvate in the Diels-Alder’s Azareaction with Cyclopentadiene

A.Yu. Aksinenko*, I.P. Kalashnikova, V.B. Sokolov

Institute of Physiologically Active Compounds of the Russian Academy of Sciences, 1 Severny proezd, Moscow region, Chernogolovka, 142432 Russia,*e-mail: alaks@ipac.ac.ru

Key words: carbamoylimines; methyltrifluoropyruvate; cyclopentadiene; [2 + 4] –cycloaddition; azanorbornenes; azabicyclo [2.2.1] heptenes; tetrahydrocyclopenta[e][1,3]oxazines

DOI: 10.18097/BMCRM00016

The whole version of this paper is available in Russian.

Carbamoylimines of methyl trifluoropyruvate react with cyclopentadiene with to formation of trifluoromethyl-containing azabicyclo [2.2.1] heptenes and tetrahydrocyclopenta[e][1,3]oxazines. NMR experiments involving DEPT and 1H{19F} determined the structure of the synthesized heterocycles and assignment of the signals in NMR spectra and established the exo-position of the CF3-group in azabicyclo[2.2.1]heptenes.

Figure 1. The scheme of reaction of N-dimethyl- and N-morpholinyl- imines of methyl trifluoropyruvate with cyclopentadiene.

Figure 2. 1H-19F correlations in the compounds 2a,b and norbornenes C and D [8].

ACKNOWLEDGEMENTS

This research was performed within the framework the government task of 2018 (Theme No. 0090-2017-0023) and was supported by the Russian Fond of Basic Research (Grants No. 16-03-00696-а).

SUPPLEMENTARY

Supplementary materials are available at http://dx.doi.org/10.18097/BMCRM00016

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