2022 vol 1 issue 1
Full paper
Magdalena Żmigrodzka1, Mikołaj Sadowski1, Jowita Kras1, Ewa Dresler2, Oleg M. Demchuk3, Karolina Kula1,4*
(1) Department of Organic Chemistry and Technology, Cracow University of Technology, Warszawska 24, 31-155 Cracow (Poland)
(2) Łukasiewicz Research Network, Institute of Heavy Organic Synthesis Blachownia Energetyków 9, 47-225 Kędzierzyn-Koźle (Poland)
(3) Laboratory of Modern Chemical Synthesis and Technology of Pharmaceutically Active Compounds, Centre for Interdisciplinary Research,
Faculty of Science and Health, The John Paul II Catholic University of Lublin, Konstantynów 1J/4.03, 20-708 Lublin (Poland)
(4) Sustainable Process Integration Laboratory, Faculty of Mechanical Engineering, Brno University of Technology, Technická 2896/2, 616 69 Brno (Czech Republic)
Correspondence to: karolina.kula@pk.edu.pl
Abstract
Pyrrolidines are important heterocyclic organic compounds which show biological effects. Many of them are successfully used in medicine. These compounds can also be applied in industry, for example as dyes or agrochemical substances. Therefore, the study of pyrrolidines chemistry is important for modern science. In this paper the pyrrolidines synthesis in [3+2] cycloaddition between N-methyl azomethine ylide and trans-3,3,3-trichloro-1-nitroprop-1-ene was studied. The reaction was carried out experimentally and based on computational research. The obtained results show the reaction may be of a polar nature, and proceed under mild conditions leading to (3SR,4RS)-1-methyl-3-nitro-4-(trichloromethyl)pyrrolidine as a single reaction product. Probably, a similar protocol can be applied for analogous reactions involving other 2-substituted nitroethene analogues.
Keywords
[3+2] cycloaddition, nitroalkenes, ylides
First published: 18.11.2022