Synthesis of novel racemic 3,4-dihydroferroceno[c]pyridines via the Ritter reaction

[Display omitted] •Racemic 3,4-dihydroferroceno[c]pyridines were obtained via the Ritter reaction.•MsOH-catalysed reaction of 2-methyl-1-ferrocenylpropan-1-ol with nitriles.•Preparative chiral HPLC resolution of the racemic 3,4-dihydroferroceno[c]pyridines.•Assignment of absolute configuration of (R...

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Bibliographic Details
Published in:Tetrahedron letters 2019-03, Vol.60 (11), p.768-772
Main Authors: Rozhkova, Yuliya S., Plekhanova, Irina V., Gorbunov, Alexey A., Stryapunina, Olga G., Chulakov, Evgeny N., Krasnov, Victor P., Ezhikova, Marina A., Kodess, Mikhail I., Slepukhin, Pavel A., Shklyaev, Yurii V.
Format: Article
Language:English
Subjects:
3,4-Dihydroferroceno[c]pyridine
Chiral HPLC
Cyclization
Nitrilium ion
Ritter reaction
X-ray diffraction
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Summary:[Display omitted] •Racemic 3,4-dihydroferroceno[c]pyridines were obtained via the Ritter reaction.•MsOH-catalysed reaction of 2-methyl-1-ferrocenylpropan-1-ol with nitriles.•Preparative chiral HPLC resolution of the racemic 3,4-dihydroferroceno[c]pyridines.•Assignment of absolute configuration of (Rp)- and (Sp)-enantiomers by X-ray. A new approach for the synthesis of functionalized racemic 3,4-dihydroferroceno[c]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-dihydroferroceno[c]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.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2019.02.009