Full Regio- and Stereoselective Protocol for the Synthesis of New Nicotinoids via Cycloaddition Processes with the Participation of Trans-Substituted Nitroethenes: Comprehensive Experimental and MEDT Study

Jowita Kras; Przemysław Woliński; Roman Nagatsky; Oleg M Demchuk; Radomir Jasiński

doi:10.3390/molecules28083535

Full Regio- and Stereoselective Protocol for the Synthesis of New Nicotinoids via Cycloaddition Processes with the Participation of Trans-Substituted Nitroethenes: Comprehensive Experimental and MEDT Study

Molecules. 2023 Apr 17;28(8):3535. doi: 10.3390/molecules28083535.

Authors

Jowita Kras¹, Przemysław Woliński¹, Roman Nagatsky¹, Oleg M Demchuk², Radomir Jasiński¹

Affiliations

¹ Department of Organic Chemistry and Technology, Cracow University of Technology, Warszawska 24, 31-155 Krakow, Poland.
² Faculty of Medicine, The John Paul II Catholic University of Lublin, Konstantynow 1J, 20-708 Lublin, Poland.

Abstract

[3 + 2] Cycloaddition reactions with the participation of Z-C-(3-pyridyl)-N-methylnitrone and series of E-2-R-nitroethenes were both experimentally and theoretically explored in the framework of Molecular Electron Density Theory. It was found that all considered processes are realized under mild conditions and in full regio- and stereocontrol. The ELF analysis additionally showed that the studied reaction proceeds by a two-stage, one-step mechanism.

Keywords: [3 + 2] cycloaddition; molecular electron density theory; nicotinoids; nitroalkenes; nitrones.

Grants and funding

This research received no external funding.