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Open Access Original article

Pathways of ion–molecular interactions of nucleogenic phenyl cations with the nucleophilic centers of picolines

Nadezhda E Shchepina1*, Viktor V Avrorin2, Gennady A Badun3, Nikolay A Bumagin4, Scott B Lewis5 and Sergey N Shurov6

Author Affiliations

1 Laboratory of Radiochemistry, Natural Sciences Institute of Perm State University, 4 Genkel St, Perm 614990, Russia

2 Chemistry Department, St-Petersburg State University, 26 Universitetsky Pr, St-Petersburg, Petrodvorets 198504, Russia

3 Radiochemistry Department, M. V. Lomonosov Moscow State University, Leninskie Gory, Moscow 119992, Russia

4 Department of Organic Chemistry, M. V. Lomonosov Moscow State University, Leninskie Gory, Moscow 119992, Russia

5 Department of Chemistry, James Madison University, Harrisonburg, VA 22807, USA

6 Department of Organic Chemistry, Perm State University, 15 Bukirev St, Perm 614990, Russia

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Organic and Medicinal Chemistry Letters 2012, 2:14  doi:10.1186/2191-2858-2-14

Published: 13 April 2012

Abstract

Background

The nuclear-chemical method brought unique opportunity for synthesis of unknown and hardly available organic compounds. Presence of tritium labeling allows one-step preparation of radioactive markers for the investigation of chemical and biological processes.

Methods

The ion–molecular reactions of nucleogenic phenyl cations with 4-picoline have been carried out. The phenyl cations were generated by spontaneous tritium β-decay within the tritium-labeled benzene. Both additions to the nitrogen and substitutions about the aromatic ring were able to be studied simultaneously.

Results

Unusual substitutions on both the α- and β-positions of the ring system have been revealed.

Conclusion

By unknown direct phenylation of nitrogen atom tritium-labeled N-phenylpicolinium derivatives, perspective biological markers have been synthesized.

Keywords:
nucleogenic phenyl cations; picoline; tritium-labeled biological markers

Graphical abstract