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Unexpected reduction of the nitro group in (3-nitrophenyl)-1,2,4-triazines during their aza-Diels–Alder reaction with 1-morpholinocyclopentene

Dmitrii Sergeevich Kopchuk 1, 2
Dmitrii Sergeevich Kopchuk
, 
Albert Faridovich Khasanov 1
Albert Faridovich Khasanov
, 
Igor Sergeevich Kovalev 1
Igor Sergeevich Kovalev
, 
Grigory Vasil'evich Zyryanov 1, 2
Grigory Vasil'evich Zyryanov
, 
Vladimir Leonidovich Rusinov 1, 2
Vladimir Leonidovich Rusinov
, 
Oleg Nikolaevich Chupakhin 1, 2
Oleg Nikolaevich Chupakhin
10.1016/j.mencom.2013.07.010
Published 2013-07-11
Communication , Volume 23, Issue 4, 209-211
23
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Kopchuk D. S. et al. Unexpected reduction of the nitro group in (3-nitrophenyl)-1,2,4-triazines during their aza-Diels–Alder reaction with 1-morpholinocyclopentene // Mendeleev Communications. 2013. Vol. 23. No. 4. pp. 209-211.
GOST all authors (up to 50) Copy
Kopchuk D. S., Khasanov A. F., Kovalev I. S., Zyryanov G. V., Rusinov V. L., Chupakhin O. N. Unexpected reduction of the nitro group in (3-nitrophenyl)-1,2,4-triazines during their aza-Diels–Alder reaction with 1-morpholinocyclopentene // Mendeleev Communications. 2013. Vol. 23. No. 4. pp. 209-211.
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TY - JOUR
DO - 10.1016/j.mencom.2013.07.010
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2013.07.010
TI - Unexpected reduction of the nitro group in (3-nitrophenyl)-1,2,4-triazines during their aza-Diels–Alder reaction with 1-morpholinocyclopentene
T2 - Mendeleev Communications
AU - Kopchuk, Dmitrii Sergeevich
AU - Khasanov, Albert Faridovich
AU - Kovalev, Igor Sergeevich
AU - Zyryanov, Grigory Vasil'evich
AU - Rusinov, Vladimir Leonidovich
AU - Chupakhin, Oleg Nikolaevich
PY - 2013
DA - 2013/07/11
PB - Mendeleev Communications
SP - 209-211
IS - 4
VL - 23
ER -
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@article{2013_Kopchuk,
author = {Dmitrii Sergeevich Kopchuk and Albert Faridovich Khasanov and Igor Sergeevich Kovalev and Grigory Vasil'evich Zyryanov and Vladimir Leonidovich Rusinov and Oleg Nikolaevich Chupakhin},
title = {Unexpected reduction of the nitro group in (3-nitrophenyl)-1,2,4-triazines during their aza-Diels–Alder reaction with 1-morpholinocyclopentene},
journal = {Mendeleev Communications},
year = {2013},
volume = {23},
publisher = {Mendeleev Communications},
month = {Jul},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2013.07.010},
number = {4},
pages = {209--211},
doi = {10.1016/j.mencom.2013.07.010}
}
MLA
Cite this
MLA Copy
Kopchuk, Dmitrii Sergeevich, et al. “Unexpected reduction of the nitro group in (3-nitrophenyl)-1,2,4-triazines during their aza-Diels–Alder reaction with 1-morpholinocyclopentene.” Mendeleev Communications, vol. 23, no. 4, Jul. 2013, pp. 209-211. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2013.07.010.

Abstract

Unexpected reduction of the nitro group to the amino one during aza-Diels–Alder reaction between (3-nitrophenyl)-1,2,4-triazines and 1-morpholinocyclopentene (neat, 200°C, argon) occurred to furnish 4-(3-aminophenyl)-6,7-dihydro-5H-cyclopenta[c]pyridines.

References

1.
1-Ethyl-1,4-dihydro-4-oxo-7-(pyridinyl)-3-quinolinecarboxylic acids. II. Synthesis
Carabateas P.M., Brundage R.P., Gelotte K.O., Gruett M.D., Lorenz R.R., Opalka C.J., Singh B., Thielking W.H., Williams G.L., Lesher G.Y.
Journal of Heterocyclic Chemistry, 1984
2.
J. Aebi, A. Binggeli, L. Green, G. Hartmann, H.P. Maerki, P. Mattei, F. Ricklin and O. Roche, Patent US2010/0016282 A1 (Chem. Abstr., 2010, 152, 192176)
3.
T. Lene and L. Janus, Patent WO2004087137 (Chem. Abstr., 2004, 141, 314334)
4.
Anilinoquinazoline Inhibitors of Fructose 1,6-Bisphosphatase Bind at a Novel Allosteric Site:  Synthesis, In Vitro Characterization, and X-ray Crystallography
Wright S.W., Carlo A.A., Carty M.D., Danley D.E., Hageman D.L., Karam G.A., Levy C.B., Mansour M.N., Mathiowetz A.M., McClure L.D., Nestor, McPherson R.K., Pandit J., Pustilnik L.R., Schulte G.K., et. al.
Journal of Medicinal Chemistry, 2002
5.
10.1016/j.mencom.2013.07.010_sbref0015a
Lui
Top. Organomet. Chem., 2010
7.
Biological labelling reagents and probes derived from luminescent transition metal polypyridine complexes
Lo K.K., Hui W., Chung C., Tsang K.H., Ng D.C., Zhu N., Cheung K.
Coordination Chemistry Reviews, 2005
8.
Design of luminescent lanthanide complexes: From molecules to highly efficient photo-emitting materials
Armelao L., Quici S., Barigelletti F., Accorsi G., Bottaro G., Cavazzini M., Tondello E.
Coordination Chemistry Reviews, 2010
10.
A Divergent SAR Study Allows Optimization of a Potent 5-HT2c Inhibitor to a Promising Antimalarial Scaffold
Calderón F., Vidal-Mas J., Burrows J., de la Rosa J.C., Jiménez-Díaz M.B., Mulet T., Prats S., Solana J., Witty M., Gamo F.J., Fernández E.
ACS Medicinal Chemistry Letters, 2012
11.
D. L. Flynn and P. A. Petillo, Patent WO2006/71940 A2 (Chem. Abstr., 2006, 145, 124558).
12.
Microwave-Assisted Suzuki Coupling Reactions with an Encapsulated Palladium Catalyst for Batch and Continuous-Flow Transformations
Baxendale I.R., Griffiths-Jones C.M., Ley S.V., Tranmer G.K.
Chemistry - A European Journal, 2006
13.
Solution, thermal and optical properties of novel poly(pyridinium salt)s derived from conjugated pyridine diamines
Nedeltchev A.K., Han H., Bhowmik P.K.
Journal of Polymer Science, Part A: Polymer Chemistry, 2010
14.
1,2,4-Triazine method of bipyridine ligand synthesis for the preparation of new luminescent Eu(III) complexes
Prokhorov A.M., Kozhevnikov V.N., Kopchuk D.S., Bernard H., Le Bris N., Tripier R., Handel H., Koenig B., Kozhevnikov D.N.
Tetrahedron, 2011
18.
5-Aryl-2,2′-bipyridines as tunable fluorophores
Kozhevnikov D.N., Shabunina O.V., Kopchuk D.S., Slepukhin P.A., Kozhevnikov V.N.
Tetrahedron Letters, 2006
19.
Synthesis of Cyclometallated Platinum Complexes with Substituted Thienylpyridines and Detailed Characterization of Their Luminescence Properties
Kozhevnikov D.N., Kozhevnikov V.N., Ustinova M.M., Santoro A., Bruce D.W., Koenig B., Czerwieniec R., Fischer T., Zabel M., Yersin H.
Inorganic Chemistry, 2009
20.
A. Nobuhiko, S. Chizu and O. Rei, Patent EP1932851 A1 (Chem. Abstr., 2006, 146, 441935).
21.
Carbazole and arylamine functionalized iridium complexes for efficient electro-phosphorescent light-emitting diodes
Wang D., Wang J., Fan H., Huang H., Chu Z., Gao X., Zou D.
Inorganica Chimica Acta, 2011
22.
Phosphorescent Mesomorphic Dyads Based on Tetraacetylethane Complexes of Iridium(III)
Prokhorov A.M., Santoro A., Williams J.A., Bruce D.W.
Angewandte Chemie - International Edition, 2011
24.
A novel synthesis of 1,2,4-triazines
Saraswathi T.V., Srinivasan V.R.
Tetrahedron Letters, 1971
25.
An efficient route to 5-(hetero)aryl-2,4′- and 2,2′-bipyridines through readily available 3-pyridyl-1,2,4-triazines
Kozhevnikov V.N., Kozhevnikov D.N., Shabunina O.V., Rusinov V.L., Chupakhin O.N.
Tetrahedron Letters, 2005
26.
From 1,2,4-triazines towards substituted pyridines and their cyclometallated Pt complexes
Kozhevnikov V.N., Ustinova M.M., Slepukhin P.A., Santoro A., Bruce D.W., Kozhevnikov D.N.
Tetrahedron Letters, 2008
27.
3-Aryl-as-triazines as potential antiinflammatory agents
O'Rourke M., Lang S.A., Cohen E.
Journal of Medicinal Chemistry, 1977
28.
An efficient route to 5,5″-diaryl-2,2′:6′,2″-terpyridines through 2,6-bis(1,2,4-triazin-3-yl)pyridines
Kozhevnikov V.N., Kozhevnikov D.N., Shabunina O.V., Rusinov V.L., Chupakhin O.N.
Tetrahedron Letters, 2005
29.
10.1016/j.mencom.2013.07.010_bib0075
Danishefsky
Chem. Ind. (London), 1967