Home / Publications / Syntheses of chiral nopinane-annelated pyridines of C2 and D2-symmetry: X-ray structures of the fused derivatives of 4,5-diazafluorene, 4,5-diaza-9H-fluoren-9-one, and 9,9’-bi-4,5-diazafluorenylidene

Syntheses of chiral nopinane-annelated pyridines of C2 and D2-symmetry: X-ray structures of the fused derivatives of 4,5-diazafluorene, 4,5-diaza-9H-fluoren-9-one, and 9,9’-bi-4,5-diazafluorenylidene

Eugene Sergeevich Vasilyev 1
Eugene Sergeevich Vasilyev
, 
Irina Yur'evna Bagryanskaya 1
Irina Yur'evna Bagryanskaya
, 
Alexey Vasil'evich Tkachev 1, 2
Alexey Vasil'evich Tkachev
10.1016/j.mencom.2017.03.006
Published 2017-02-27
Communication , Volume 27, Issue 2, 128-130
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Vasilyev E. S., Bagryanskaya I. Y., Tkachev A. V. Syntheses of chiral nopinane-annelated pyridines of C2 and D2-symmetry: X-ray structures of the fused derivatives of 4,5-diazafluorene, 4,5-diaza-9H-fluoren-9-one, and 9,9’-bi-4,5-diazafluorenylidene // Mendeleev Communications. 2017. Vol. 27. No. 2. pp. 128-130.
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Vasilyev E. S., Bagryanskaya I. Y., Tkachev A. V. Syntheses of chiral nopinane-annelated pyridines of C2 and D2-symmetry: X-ray structures of the fused derivatives of 4,5-diazafluorene, 4,5-diaza-9H-fluoren-9-one, and 9,9’-bi-4,5-diazafluorenylidene // Mendeleev Communications. 2017. Vol. 27. No. 2. pp. 128-130.
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TY - JOUR
DO - 10.1016/j.mencom.2017.03.006
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2017.03.006
TI - Syntheses of chiral nopinane-annelated pyridines of C2 and D2-symmetry: X-ray structures of the fused derivatives of 4,5-diazafluorene, 4,5-diaza-9H-fluoren-9-one, and 9,9’-bi-4,5-diazafluorenylidene
T2 - Mendeleev Communications
AU - Vasilyev, Eugene Sergeevich
AU - Bagryanskaya, Irina Yur'evna
AU - Tkachev, Alexey Vasil'evich
PY - 2017
DA - 2017/02/27
PB - Mendeleev Communications
SP - 128-130
IS - 2
VL - 27
ER -
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@article{2017_Vasilyev,
author = {Eugene Sergeevich Vasilyev and Irina Yur'evna Bagryanskaya and Alexey Vasil'evich Tkachev},
title = {Syntheses of chiral nopinane-annelated pyridines of C2 and D2-symmetry: X-ray structures of the fused derivatives of 4,5-diazafluorene, 4,5-diaza-9H-fluoren-9-one, and 9,9’-bi-4,5-diazafluorenylidene},
journal = {Mendeleev Communications},
year = {2017},
volume = {27},
publisher = {Mendeleev Communications},
month = {Feb},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2017.03.006},
number = {2},
pages = {128--130},
doi = {10.1016/j.mencom.2017.03.006}
}
MLA
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Vasilyev, Eugene Sergeevich, et al. “Syntheses of chiral nopinane-annelated pyridines of C2 and D2-symmetry: X-ray structures of the fused derivatives of 4,5-diazafluorene, 4,5-diaza-9H-fluoren-9-one, and 9,9’-bi-4,5-diazafluorenylidene.” Mendeleev Communications, vol. 27, no. 2, Feb. 2017, pp. 128-130. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2017.03.006.

Abstract

Reaction of (+)-pinocarvone oxime with 2-morpholinocyclopent-2-enone and FeCl3·6H2O affords chiral C2-symmetric fused derivative of 4,5-diazafluorene, whose oxidation with SeO2 gives nopinane-annelated derivatives of 4,5-diaza-9Hfluoren- 9-one (C2-symmetry) and of 9,9’-bi-4,5-diazafluorenylidene (D2-symmetry). Structures of the compounds synthesized were proved by X-ray crystallography.

References

4.
Helical Chiral PyridineN-Oxides: A New Family of Asymmetric Catalysts
Chen J., Takenaka N.
Chemistry - A European Journal, 2009
7.
Chiral 2,2‘-Bipyridine-Type N-Monoxides as Organocatalysts in the Enantioselective Allylation of Aldehydes with Allyltrichlorosilane
Malkov A.V., Orsini M., Pernazza D., Muir K.W., Langer V., Meghani P., Kočovský P.
Organic Letters, 2002
8.
Chiral N‐Oxides in Asymmetric Catalysis
Malkov A.V., Kočovský P.
European Journal of Organic Chemistry, 2006
10.
Chiral zinc(II) and cadmium(II) complexes with a dihydrophenanthroline ligand bearing (–)-α-pinene fragments: Synthesis, crystal structures and photophysical properties
Kokina T.E., Glinskaya L.A., Tkachev A.V., Plyusnin V.F., Tsoy Y.V., Bagryanskaya I.Y., Vasilyev E.S., Piryazev D.A., Sheludyakova L.A., Larionov S.V.
Polyhedron, 2016
12.
Synthesis of 2-hydroxy-3-methylcyclopent-2-en-1-one. III
Sato K., Inoue S., Kitagawa T., Takahashi T.
Journal of Organic Chemistry, 1973
13.
Vasilyev E.S., Agafontsev A.M., Kolesnik V.D., Gatilov Y.V., Tkachev A.V.
Mendeleev Communications, 2011
16.
10.1016/j.mencom.2017.03.006_bib0050
Sheldrick
SHELX-97, Programs for Crystal Structure Analysis (Release 97-2), 1997
17.
10.1016/j.mencom.2017.03.006_sbref0055a
Spek
PLATON, A Multipurpose Crystallographic Tool (Version 10M), 2003
18.
Single-crystal structure validation with the programPLATON
Spek A.L.
Journal of Applied Crystallography, 2003