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A rational protocol for the synthesis of 1-(2-pyridyl)isoquinolines

Dmitrii Sergeevich Kopchuk 1, 2
Dmitrii Sergeevich Kopchuk
Igor Sergeevich Kovalev 1
Igor Sergeevich Kovalev
Albert Faridovich Khasanov 1
Albert Faridovich Khasanov
Grigory Vasil'evich Zyryanov 1, 2
Grigory Vasil'evich Zyryanov
Pavel Alexandrovich Slepukhin 2
Pavel Alexandrovich Slepukhin
Vladimir Leonidovich Rusinov 1, 2
Vladimir Leonidovich Rusinov
Oleg Nikolaevich Chupakhin 1, 2
Oleg Nikolaevich Chupakhin
Published 2013-05-08
CommunicationVolume 23, Issue 3, 142-144
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Kopchuk D. S. et al. A rational protocol for the synthesis of 1-(2-pyridyl)isoquinolines // Mendeleev Communications. 2013. Vol. 23. No. 3. pp. 142-144.
GOST all authors (up to 50) Copy
Kopchuk D. S., Kovalev I. S., Khasanov A. F., Zyryanov G. V., Slepukhin P. A., Rusinov V. L., Chupakhin O. N. A rational protocol for the synthesis of 1-(2-pyridyl)isoquinolines // Mendeleev Communications. 2013. Vol. 23. No. 3. pp. 142-144.
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TY - JOUR
DO - 10.1016/j.mencom.2013.05.007
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2013.05.007
TI - A rational protocol for the synthesis of 1-(2-pyridyl)isoquinolines
T2 - Mendeleev Communications
AU - Kopchuk, Dmitrii Sergeevich
AU - Kovalev, Igor Sergeevich
AU - Khasanov, Albert Faridovich
AU - Zyryanov, Grigory Vasil'evich
AU - Slepukhin, Pavel Alexandrovich
AU - Rusinov, Vladimir Leonidovich
AU - Chupakhin, Oleg Nikolaevich
PY - 2013
DA - 2013/05/08
PB - Mendeleev Communications
SP - 142-144
IS - 3
VL - 23
ER -
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@article{2013_Kopchuk,
author = {Dmitrii Sergeevich Kopchuk and Igor Sergeevich Kovalev and Albert Faridovich Khasanov and Grigory Vasil'evich Zyryanov and Pavel Alexandrovich Slepukhin and Vladimir Leonidovich Rusinov and Oleg Nikolaevich Chupakhin},
title = {A rational protocol for the synthesis of 1-(2-pyridyl)isoquinolines},
journal = {Mendeleev Communications},
year = {2013},
volume = {23},
publisher = {Mendeleev Communications},
month = {May},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2013.05.007},
number = {3},
pages = {142--144},
doi = {10.1016/j.mencom.2013.05.007}
}
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Cite this
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Kopchuk, Dmitrii Sergeevich, et al. “A rational protocol for the synthesis of 1-(2-pyridyl)isoquinolines.” Mendeleev Communications, vol. 23, no. 3, May. 2013, pp. 142-144. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2013.05.007.

Abstract

Aza-Diels–Alder reaction between 3-(2-pyridyl)-1,2,4-triazines and 1-morpholinocyclohexene followed by aromatization of the cyclohexene moiety affords 1-(2-pyridyl)isoquinolines. Crystal structures of two tetrahydroisoquinolines were confirmed by X-ray diffraction analysis.

References

1.
10.1016/j.mencom.2013.05.007_sbref0005a
Pijper
Eur. J. Med. Chem., 1984
2.
Quinoline- and isoquinoline-sulfonamide derivatives of LCAP as potent CNS multi-receptor—5-HT1A/5-HT2A/5-HT7 and D2/D3/D4—agents: The synthesis and pharmacological evaluation
Zajdel P., Marciniec K., Maślankiewicz A., Satała G., Duszyńska B., Bojarski A.J., Partyka A., Jastrzębska-Więsek M., Wróbel D., Wesołowska A., Pawłowski M.
Bioorganic and Medicinal Chemistry, 2012
4.
The Chemistry of Heterocyclic Compounds: Isoquinolines, eds. G. M. Coppola and H. F. Schuster, Wiley, New York, 1981, vol. 38, part 3.
5.
Asymmetric Synthesis of Isoquinoline Alkaloids
Chrzanowska M., Rozwadowska M.D.
Chemical Reviews, 2004
6.
Anti-HIV benzylisoquinoline alkaloids and flavonoids from the leaves of Nelumbo nucifera, and structure–activity correlations with related alkaloids
Kashiwada Y., Aoshima A., Ikeshiro Y., Chen Y., Furukawa H., Itoigawa M., Fujioka T., Mihashi K., Cosentino L.M., Morris-Natschke S.L., Lee K.
Bioorganic and Medicinal Chemistry, 2005
7.
Ligands of the Peripheral Benzodiazepine Receptor Are Potent Inhibitors of Plasmodium falciparum and Toxoplasma gondii In Vitro
Dzierszinski F., Coppin A., Mortuaire M., Dewailly E., Slomianny C., Ameisen J., DeBels F., Tomavo S.
Antimicrobial Agents and Chemotherapy, 2002
8.
Synthesis and Radioligand Binding Studies of Bis-isoquinolinium Derivatives as Small Conductance Ca2+-Activated K+ Channel Blockers
Graulich A., Dilly S., Farce A., Scuvée-Moreau J., Waroux O., Lamy C., Chavatte P., Seutin V., Liégeois J.
Journal of Medicinal Chemistry, 2007
9.
Synthesis and dopamine agonist and antagonist effects of (R)-(-)- and (S)-(+)-11-hydroxy-N-n-propylnoraporphine
Gao Y., Zong R., Campbell A., Kula N.S., Baldessarini R.J., Neumeyer J.L.
Journal of Medicinal Chemistry, 1988
11.
The Pyrrolo[2,1-a]isoquinoline Alkaloids
Pässler U., Knölker H.
Alkaloids: Chemistry and Biology, 2011
13.
Zinc-Specific Fluorescent Response of Tris(isoquinolylmethyl)amines (isoTQAs)
Mikata Y., Kawata K., Iwatsuki S., Konno H.
Inorganic Chemistry, 2012
14.
Practical Preparation and Resolution of 1-(2‘-Diphenylphosphino-1‘-naphthyl)isoquinoline:  A Useful Ligand for Catalytic Asymmetric Synthesis
Lim C.W., Tissot O., Mattison A., Hooper M.W., Brown J.M., Cowley A.R., Hulmes D.I., Blacker A.J.
Organic Process Research and Development, 2003
16.
π-Conjugated Chelating Polymers with Charged Iridium Complexes in the Backbones: Synthesis, Characterization, Energy Transfer, and Electrochemical Properties
17.
Homoleptic Cyclometalated Iridium Complexes with Highly Efficient Red Phosphorescence and Application to Organic Light-Emitting Diode
Tsuboyama A., Iwawaki H., Furugori M., Mukaide T., Kamatani J., Igawa S., Moriyama T., Miura S., Takiguchi T., Okada S., Hoshino M., Ueno K.
Journal of the American Chemical Society, 2003
18.
J. Y. Lee, Y.J. Choi, J.H. Kwon and H. K. Chung, U.S. Patent 20050112401A1, 2005.(Chem. Abstr., 2005, 142, 490492).
22.
�ber eine neue Isochinolinsynthese
Pomeranz C.
Monatshefte fur Chemie, 1893
24.
A General Solution for Unstable Boronic Acids: Slow-Release Cross-Coupling from Air-Stable MIDA Boronates
Knapp D.M., Gillis E.P., Burke M.D.
Journal of the American Chemical Society, 2009
25.
Heteroaryl Cross-Coupling as an Entry toward the Synthesis of Lavendamycin Analogues: A Model Study
Verniest G., Wang X., Kimpe N.D., Padwa A.
Journal of Organic Chemistry, 2009
26.
M. P. Arend, L.A. Flippin, V. Guenzler-Pukall, W.-B. Ho, E.D. Turtle and X. Du, US Patent 254215A1, 2004 (Chem. Abstr., 2004, 142, 56195).
29.
ANALOGUES OF 2,2′-BIPYRIDYL WITH ISOQUINOLINE AND THIAZOLE RINGS. PART I
Knott R.F., Breckenridge J.G.
Canadian Journal of Chemistry, 1954
34.
Rhodium-catalyzed oxidative coupling of aromatic imines with internal alkynes via regioselective C–H bond cleavage
35.
Synthesis of isoquinolines by cycloaddition of arynes to 1,2,4-triazines
Gonsalves A.M., Pinho e Melo T.M., Gilchrist T.L.
Tetrahedron, 1992
39.
Aryne intermediates in the synthesis of polynuclear heterocyclic systems (Review)
Kovalev I.S., Kopchuk D.S., Zyryanov G.V., Slepukhin P.A., Rusinov V.L., Chupakhin O.N.
Chemistry of Heterocyclic Compounds, 2012
40.
D. S. Kopchuk, G.V. Zyryanov, I.S. Kovalev, I.N. Egorov, V.L. Rusinov and O. N. Chupakhin, Khim. Geterotsikl. Soedin., 2012, 1994.(in Russian).
45.
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
46.
2,2′-Bipyridinyl carboranes as B,N,N-ligands in cyclometallated complexes of platinum(ii)
Prokhorov A.M., Slepukhin P.A., Rusinov V.L., Kalinin V.N., Kozhevnikov D.N.
Chemical Communications, 2011
47.
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
48.
3-Aryl-as-triazines as potential antiinflammatory agents
O'Rourke M., Lang S.A., Cohen E.
Journal of Medicinal Chemistry, 1977
52.
Novel method for the synthesis of pyrido[2,3-d]pyrimidine-2,4-diones from 5,7-dimethylpyrimido[4,5-e]-1,2,4-triazine-6,8-dione
Shorshnev S.V., Chernyshev A.I., Esipov S.E., Pozharskii A.F., Kuz'menko V.V., Gulevskaya A.V.
Chemistry of Heterocyclic Compounds, 1987
54.
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
55.
Dehydrogenation of polycyclic hydroaromatic compounds
56.
A Rational Protocol for the Synthesis of Arylated Bipyridine Ligands via a Cycloaddition Pathway
57.
The analytical calculation of absorption in multifaceted crystals
Clark R.C., Reid J.S.
Acta Crystallographica Section A Foundations of Crystallography, 1995
58.
A short history of SHELX
Sheldrick G.M.
Acta Crystallographica Section A Foundations of Crystallography, 2007