Hydroxypropyl substituted nitrogen bridgehead fused cyanopyridines

The reaction of 2-hetaryl-2-(tetrahydro-2-furanyliden)acetonitriles with substituted acetonitriles as C-nucleophiles has been investigated and the mechanism of the reaction has been suggested. A base promoted Michael addition of the substituted acetonitriles to 2-hetaryl-2-(tetrahydro-2-furanyliden)...

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Bibliographic Details
Published in:Tetrahedron 2014-02, Vol.70 (6), p.1214-1222
Main Authors: Milokhov, Demyd S., Khilya, Olga V., Turov, Alexander V., Medviediev, Volodymyr V., Shishkin, Oleg V., Volovenko, Yulian M.
Format: Article
Language:English
Subjects:
2-Hetaryl-2-(tetrahydro-2-furanyliden)acetonitriles
Acetonitrile
Bearing
Chains
Diffraction
Fused pyridines
Hetarylacetonitriles
Michael addition
NMR spectroscopy
Nucleophiles
Tetrahedrons
Transformations
X-rays
ω-Hydroxyalkylheterocycles
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Summary:The reaction of 2-hetaryl-2-(tetrahydro-2-furanyliden)acetonitriles with substituted acetonitriles as C-nucleophiles has been investigated and the mechanism of the reaction has been suggested. A base promoted Michael addition of the substituted acetonitriles to 2-hetaryl-2-(tetrahydro-2-furanyliden)acetonitriles followed by ring transformations has provided novel convenient synthetic methods to nitrogen bridgehead fused cyanopyridines bearing hydroxypropyl side chain. The structures of obtained compounds have been established based on NMR spectroscopy investigation and X-ray diffraction data. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2013.12.074