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Synthesis of novel racemic 3,4-dihydroferroceno[c]pyridines via the Ritter reaction |
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| Authors: | Yuliya S Rozhkova Irina V Plekhanova Alexey A Gorbunov Olga G Stryapunina Evgeny N Chulakov Victor P Krasnov Marina A Ezhikova Mikhail I Kodess Pavel A Slepukhin Yurii V Shklyaev |
| Institution: | 1. Institute of Technical Chemistry, Russian Academy of Sciences (Ural Branch), 3 Akademika Korolyeva St., Perm 614013, Russia;2. Perm State University, 15 Bukireva St., Perm 614990, Russia;3. Postovsky Institute of Organic Synthesis, Russian Academy of Sciences (Ural Branch), 22 S Kovalevskoy St., Ekaterinburg 620990, Russia;4. Ural Federal University, 19 Mira St., Ekaterinburg 620002, Russia |
| Abstract: | A new approach for the synthesis of functionalized racemic 3,4-dihydroferrocenoc]pyridines via the Ritter reaction of 2-methyl-1-ferrocenylpropan-1-ol with nitriles in the presence of methansulfonic acid was developed. The scope and limitations of the reaction were evaluated. Selected racemic 3,4-dihydroferrocenoc]pyridines were successfully separated by preparative HPLC on a Chiralcel OD-H column. The absolute configuration of the enantiomers was determined by X-ray crystal structure analysis. |
| Keywords: | Ritter reaction Nitrilium ion Cyclization Chiral HPLC X-ray diffraction |
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