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

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.
Source :: Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry. Mar2019, Vol. 60 Issue 11, p768-772. 5p.
Publication Year :: 2019
Abstract: Graphical abstract Highlights • 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 p)- and (S p)-enantiomers by X-ray. Abstract 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. [ABSTRACT FROM AUTHOR]

Subjects :: *PYRIDINE synthesis
*TARTARIC acid
*HIGH performance liquid chromatography
*CHEMICAL reactions
*ENANTIOMERS

Language :: English
ISSN :: 00404039
Volume :: 60
Issue :: 11
Database :: Academic Search Index
Journal :: Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry
Publication Type :: Academic Journal
Accession number :: 134904439
Full Text :: https://doi.org/10.1016/j.tetlet.2019.02.009

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