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Stereoselective functionalisation of pinopyridine with anisidines and o-phenylenediamine

Eugene Sergeevich Vasilyev 1
Eugene Sergeevich Vasilyev
, 
Alexander Mikhailovich Agafontsev 1
Alexander Mikhailovich Agafontsev
, 
Vasilii Dmitrievich Kolesnik 1
Vasilii Dmitrievich Kolesnik
, 
Yuriy Vasil'evich Gatilov 1
Yuriy Vasil'evich Gatilov
, 
Alexey Vasil'evich Tkachev 1, 2
Alexey Vasil'evich Tkachev
10.1016/j.mencom.2011.09.007
Published 2011-09-14
Communication , Volume 21, Issue 5, 253-255
4
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Vasilyev E. S. et al. Stereoselective functionalisation of pinopyridine with anisidines and o-phenylenediamine // Mendeleev Communications. 2011. Vol. 21. No. 5. pp. 253-255.
GOST all authors (up to 50) Copy
Vasilyev E. S., Agafontsev A. M., Kolesnik V. D., Gatilov Y. V., Tkachev A. V. Stereoselective functionalisation of pinopyridine with anisidines and o-phenylenediamine // Mendeleev Communications. 2011. Vol. 21. No. 5. pp. 253-255.
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TY - JOUR
DO - 10.1016/j.mencom.2011.09.007
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2011.09.007
TI - Stereoselective functionalisation of pinopyridine with anisidines and o-phenylenediamine
T2 - Mendeleev Communications
AU - Vasilyev, Eugene Sergeevich
AU - Agafontsev, Alexander Mikhailovich
AU - Kolesnik, Vasilii Dmitrievich
AU - Gatilov, Yuriy Vasil'evich
AU - Tkachev, Alexey Vasil'evich
PY - 2011
DA - 2011/09/14
PB - Mendeleev Communications
SP - 253-255
IS - 5
VL - 21
ER -
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@article{2011_Vasilyev,
author = {Eugene Sergeevich Vasilyev and Alexander Mikhailovich Agafontsev and Vasilii Dmitrievich Kolesnik and Yuriy Vasil'evich Gatilov and Alexey Vasil'evich Tkachev},
title = {Stereoselective functionalisation of pinopyridine with anisidines and o-phenylenediamine},
journal = {Mendeleev Communications},
year = {2011},
volume = {21},
publisher = {Mendeleev Communications},
month = {Sep},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2011.09.007},
number = {5},
pages = {253--255},
doi = {10.1016/j.mencom.2011.09.007}
}
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Vasilyev, Eugene Sergeevich, et al. “Stereoselective functionalisation of pinopyridine with anisidines and o-phenylenediamine.” Mendeleev Communications, vol. 21, no. 5, Sep. 2011, pp. 253-255. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2011.09.007.

Abstract

Benzylic oxidation of pinopyridine with SeO2 affords the corresponding keto derivative (71% yield) whose reductive amination with o- and p-anisidines proceeds stereoselectively to give 8R-amino derivatives; the reaction with o-phenylenediamine results in achiral pyridophenazine derivative possessing intense blue fluorescence at 441nm. Structures of o-anisidine derivative and substituted pyridophenazine have been characterized by X-ray crystallography.

References

1.
Metal complexes of chiral pyridine ligands. X-ray structure of nitratobis {2-(2S)-2-pyrrolidinyl]pyridine} copper (II) nitrate
Bacchi A., Chelucci G., Grandino M., Minardi G., Pelizzi C., Pelizzi G., Solinas C.
Journal of Chemical Crystallography, 1994
3.
Stereoselective synthesis of coordination compounds
von Zelewsky A.
Coordination Chemistry Reviews, 1999
4.
Chiral pyridine-containing ligands in asymmetric catalysis
KWONG H., YEUNG H., YEUNG C., LEE W., LEE C., WONG W.
Coordination Chemistry Reviews, 2007
5.
Chiral N‐Oxides in Asymmetric Catalysis
Malkov A.V., Kočovský P.
European Journal of Organic Chemistry, 2006
6.
10.1016/j.mencom.2011.09.007_bib0015
Doyle
Modern Catalytic Methods for Organic Synthesis with Diazo Compounds, 1998
9.
New pyridine N-oxides as chiral organocatalysts in the asymmetric allylation of aromatic aldehydes
Malkov A.V., Westwater M., Gutnov A., Ramírez-López P., Friscourt F., Kadlčíková A., Hodačová J., Rankovic Z., Kotora M., Kočovský P.
Tetrahedron, 2008
13.
Chiral Pyridine-Based Macrobicyclic Clefts:  Synthesis and Enantiomeric Recognition of Ammonium Salts
Hellier P.C., Bradshaw J.S., Young J.J., Zhang X.X., Izatt R.M.
Journal of Organic Chemistry, 1996
14.
Flexible Bidentate Pyridine and Chiral Ligands in the Self-Assembly of Supramolecular 3-D Cages
Chi K., Addicott C., Kryschenko Y.K., Stang P.J.
Journal of Organic Chemistry, 2004
15.
New chiral pyrazine-based ligands for self-assembly reactions
Bark T., Stoeckli-Evans H., Zelewsky A.V.
Journal of the Chemical Society Perkin Transactions 1, 2002
16.
Enantiomerically Pure Chiral Coordination Polymers:  Synthesis, Spectroscopy, and Electrochemistry in Solution and on Surfaces
Bernhard S., Takada K., Díaz D.J., Abruña H.D., Mürner H.
Journal of the American Chemical Society, 2001