Pyridines and pyridine derivatives from vinyl allenes and imines

The Lewis acid mediated reaction of acyclic vinyl allenes and imines, yielding tetrahydropyridines has been carried out. Only one cycloadduct was observed in each case, and thus, the reaction progressed in all cases with total regio-, face- and endo/exo selectivities. The cycloadducts were transform...

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Bibliographic Details
Published in:Tetrahedron 2012-11, Vol.68 (46), p.9345-9349
Main Authors: Regás, David, Afonso, María M., Palenzuela, J. Antonio
Format: Article
Language:English
Subjects:
Alicyclic compounds
Alicyclic compounds, terpenoids, prostaglandins, steroids
Allenes
Catalysis
Chemistry
Dehydrogenation
Derivatives
Diels–Alder
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Heterocyclic compounds with several n hetero atoms in the same ring, in separated rings or in fused rings
Hydrogen storage
Hydrogenation
Imines
Lewis acid
Organic chemistry
Preparations and properties
Pyridines
Tetrahedrons
Tetrahydroquinolines
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Summary:The Lewis acid mediated reaction of acyclic vinyl allenes and imines, yielding tetrahydropyridines has been carried out. Only one cycloadduct was observed in each case, and thus, the reaction progressed in all cases with total regio-, face- and endo/exo selectivities. The cycloadducts were transformed into polysubstituted pyridines, including bipyridines, by catalytic transfer hydrogenation using cyclohexene as hydrogen donor in good yield. The reaction was extended to the aromatization of the bicyclic cycloadducts prepared in previous works from the reaction of semicyclic vinyl allenes and imines, yielding tetrahydropyridines. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2012.09.057