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Nucleophilic aromatic substitution of hydrogen and related reactions

Valery Nikolaevich Charushin 1, 2
Valery Nikolaevich Charushin
, 
Oleg Nikolaevich Chupakhin 1, 2
Oleg Nikolaevich Chupakhin
10.1016/j.mencom.2007.09.001
Published 2007-09-12
Focus article , Volume 17, Issue 5, 249-254
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Charushin V. N., Chupakhin O. N. Nucleophilic aromatic substitution of hydrogen and related reactions // Mendeleev Communications. 2007. Vol. 17. No. 5. pp. 249-254.
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Charushin V. N., Chupakhin O. N. Nucleophilic aromatic substitution of hydrogen and related reactions // Mendeleev Communications. 2007. Vol. 17. No. 5. pp. 249-254.
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TY - JOUR
DO - 10.1016/j.mencom.2007.09.001
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2007.09.001
TI - Nucleophilic aromatic substitution of hydrogen and related reactions
T2 - Mendeleev Communications
AU - Charushin, Valery Nikolaevich
AU - Chupakhin, Oleg Nikolaevich
PY - 2007
DA - 2007/09/12
PB - Mendeleev Communications
SP - 249-254
IS - 5
VL - 17
ER -
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@article{2007_Charushin,
author = {Valery Nikolaevich Charushin and Oleg Nikolaevich Chupakhin},
title = {Nucleophilic aromatic substitution of hydrogen and related reactions},
journal = {Mendeleev Communications},
year = {2007},
volume = {17},
publisher = {Mendeleev Communications},
month = {Sep},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2007.09.001},
number = {5},
pages = {249--254},
doi = {10.1016/j.mencom.2007.09.001}
}
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Charushin, Valery Nikolaevich, and Oleg Nikolaevich Chupakhin. “Nucleophilic aromatic substitution of hydrogen and related reactions.” Mendeleev Communications, vol. 17, no. 5, Sep. 2007, pp. 249-254. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2007.09.001.
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Abstract

The classical concept of nucleophilic aromatic substitution (SNAripso) has been complemented with a new synthetic methodology (SNH), enabling one to build new carbon–carbon C(sp2)–C(sp3), C(sp2)–C(sp2) and C(sp2)–C(sp) or carbon–heteroatom C(sp2)–X (X is O, N, P, S, halogen) bonds through nucleophilic displacement of hydrogen in an aromatic ring.

References

1.
10.1016/j.mencom.2007.09.001_bib1
Chupakhin
Nucleophilic Aromatic Substitution of Hydrogen, 1994
2.
Nucleophilic Substitution of Hydrogen in Aromatic Systems
Chupakhin O.N., Postovskii I.Y.
Russian Chemical Reviews, 1976
3.
10.1016/j.mencom.2007.09.001_bib3
van der Plas
Croat. Chem. Acta, 1986
4.
Vicarious nucleophilic substitution of hydrogen
Makosza M., Winiarski J.
Accounts of Chemical Research, 1987
5.
Nucleophilic substitution of hydrogen in azines
Chupakhin O.N., Charushin V.N., van der Plas H.C.
Tetrahedron, 1988
7.
10.1016/j.mencom.2007.09.001_bib7
Terrier
1991
8.
10.1016/j.mencom.2007.09.001_bib8
Makosza
Pol. J. Chem., 1992
9.
10.1016/j.mencom.2007.09.001_bib9
Makosza
Izv. Akad. Nauk, Ser. Khim., 1996
10.
1,2,4-TriazineN-oxides and their annelated derivatives
Kozhevnikov D.N., Rusinov V.L., Chupakhin O.N.
Russian Chemical Reviews, 1998
11.
10.1016/j.mencom.2007.09.001_bib11
Gulevskaya
Targets in Heterocyclic Systems, 1999
12.
10.1016/j.mencom.2007.09.001_bib12
Kozhevnikov
Adv. Heterocycl. Chem., 2002
14.
SNH methodology and new approaches to condensed heterocyclic systems
Charushin V.N., Chupakhin O.N.
Pure and Applied Chemistry, 2004
15.
Nucleophilic Substitution of Hydrogen in Heterocyclic Chemistry
Ma̧kosza M., Wojciechowski K.
Chemical Reviews, 2004
16.
10.1016/j.mencom.2007.09.001_bib16
Chupakhin
INCA, 2005
17.
Asymmetric induction in the nucleophilic addition in the series of aromatic azines
Egorov I.N., Zyryanov G.V., Rusinov V.L., Chupakhin O.N.
Russian Chemical Reviews, 2005
18.
Progress in the studies of oxidation of dihydropyridines and their analogues
Matern A.I., Charushin V.N., Chupakhin O.N.
Russian Chemical Reviews, 2007
19.
10.1016/j.mencom.2007.09.001_bib19
Morrison
Organic Chemistry, 1970
20.
10.1016/j.mencom.2007.09.001_bib20
Arends
Green Chemistry and Catalysis, 2007
21.
10.1016/j.mencom.2007.09.001_bib21
2005
22.
Consecutive nucleophilic substitution and aza Diels–Alder reaction—an efficient strategy to functionalized 2,2′-bipyridines
Kozhevnikov D.N., Kozhevnikov V.N., Prokhorov A.M., Ustinova M.M., Rusinov V.L., Chupakhin O.N., Aleksandrov G.G., König B.
Tetrahedron Letters, 2006
25.
Deoxygenative vs. Vicarious Nucleophilic Substitution of Hydrogen in Reactions of 1,2,4-Triazine 4-Oxides with α-Halocarbanions
Kozhevnikov D., Rusinov V., Chupakhin O., Makosza M., Rykowski A., Wolinska E.
European Journal of Organic Chemistry, 2002
26.
10.1016/j.mencom.2007.09.001_bib25
Pozharsky
Aminirovanie geterotsiklov po Chichibabinu (Chichibabin Amination of Heterocycles), 1971
27.
The .sigma. adducts of 5-nitropyrimidines with liquid ammonia and their oxidation into aminonitropyrimidines
Van der Plas H.C., Charushin V.N., Van Veldhuizen B.
Journal of Organic Chemistry, 1983
29.
Carborane-Functionalized Polyaza Aromatic Ligands:  Synthesis, Crystal Structure, and a Copper(II) Complex
Prokhorov A.M., Kozhevnikov D.N., Rusinov V.L., Chupakhin O.N., Glukhov I.V., Antipin M.Y., Kazheva O.N., Chekhlov A.N., Dyachenko O.A.
Organometallics, 2006
30.
Direct C–C Coupling of Ferrocenyllithium and Azaheterocycles by Nucleophilic Substitution of Hydrogen – Synthesis of Mono- and 1,1′-Diazinylferrocenes
Chupakhin O.N., Utepova I.A., Kovalev I.S., Rusinov V.L., Starikova Z.A.
European Journal of Organic Chemistry, 2007
31.
An unusual aromatisation of dihydropyrimidines facilitated by reduction of the nitro group
Rusinov G.L., Gorbunov E.B., Charushin V.N., Chupakhin O.N.
Tetrahedron Letters, 2007
32.
One-Step Heterylation at the Upper Rim of Calix[4]arene with 1,2,4-Triazin-5(2H)-ones
Beresnev D.G., Itsikson N.A., Chupakhin O.N., Charushin V.N., Kodess M.I., Butakov A.I., Rusinov G.L., Morzherin Y.Y., Konovalov A.I., Antipin I.S.
Journal of Organic Chemistry, 2006
33.
10.1016/j.mencom.2007.09.001_bib31_1
Chupakhin
Izv. Akad. Nauk, Ser. Khim., 2004
34.
10.1016/j.mencom.2007.09.001_bib31_2
Chupakhin
Izv. Akad. Nauk, Ser. Khim., 2004
35.
Direct C-C Coupling of meso-Octamethylcalix[4]pyrrole with 6-Nitroazolopyrimidines
N. Chupakhin O., A. Itsikson N., Sh. Bashirov S., G. Beresnev D., L. Rusinov G.
Heterocycles, 2005
37.
15th European Symposium on Organic Chemistry (ESOC 15), Dublin, Ireland
Lloyd-Jones G.C., Paz Muñoz M., Owen-Smith G.
European Journal of Organic Chemistry, 2007
38.
Chupakhin O.N., Azev Y.A., Alexeev S.G., Shorshnev S.V., Tsoi E., Charushin V.N.
Mendeleev Communications, 1992
39.
Chupakhin O.N., Beresnev D.G., Itsikson N.A.
Mendeleev Communications, 2006
40.
The Reactions of Azines on Treatment with 1,3-Bifunctional Nucleophiles
Charushin V.N., Chupakhin O.N.
Russian Chemical Reviews, 1984
41.
Reactions of Azines with Bifunctional Nucleophiles: Cyclizations and Ring Transformations
Charushin V.N., Chupakhin O.N., Van Der Plas H.C.
Advances in Heterocyclic Chemistry, 1988
43.
Charushin V.N., Mokrushina G.A., Petrova G.M., Alexandrov G.G., Chupakhin O.N.
Mendeleev Communications, 1998
44.
Application of 1H, 13C and 15N NMR in the chemistry of 1,4-diazines
Chupakhin O.N., Charushin V.N., Chernyshev A.I.
Progress in Nuclear Magnetic Resonance Spectroscopy, 1988
45.
Application of1H and13C NMR to the structural elucidation of tetrahydroquinoxalines condensed with five-membered heterocycles
Charushin V.N., Chernyshev A.I., Sorokin N.N., Chupakhin O.N.
Magnetic Resonance in Chemistry, 1984
46.
1H and13C NMR spectra of tetrahydroquinoxalines condensed with six-membered heterocycles
Charushin V.N., Sorokin N.N., Chernyshev A.I., Baklykov V.G., Ponizovsky M.G., Chupakhin O.N.
Magnetic Resonance in Chemistry, 1986
47.
Rusinov G.L., Slepukhin P.A., Charushin V.N., Dyachenko O.A., Kazheva O.N., Chekhlov A.N., Verbitsky E.V., Kodess M.I., Chupakhin O.N.
Mendeleev Communications, 2006
48.
Rusinov G.L., Slepukhin P.A., Charushin V.N., Chupakhin O.N.
Mendeleev Communications, 2001
49.
Behavior of Monocyclic 1,2,4-Triazines in Reactions with C-, N-, O-, and S-Nucleophiles
Charushin V.N., Alexeev S.G., Chupahkin O.N., Van Der Plas H.C.
Advances in Heterocyclic Chemistry, 1989
50.
Cyclizations of 1,2,4-triazinium salts with bifunctional nucleophiles - a new route to condensed 1,2,4-triazines
Alexeev S.G., Charushin V.N., Chupakhin O.N., Alexandrov G.G.
Tetrahedron Letters, 1988
51.
10.1016/j.mencom.2007.09.001_bib39_3
Prokhorov
Pol. J. Chem., 2003
52.
N. Chupakhin O., Chupakhin O., Alexeev S., Rudakov B., Charushin V.
Heterocycles, 1992
53.
A simple one pot synthesis of condensed 1,2,4-triazines by using the tandem aN-SNipsoand SNH-SNipsareactions
Chupakhin O.N., Rusinov G.L., Beresnev D.G., Charushin V.N., Neunhoeffer H.
Journal of Heterocyclic Chemistry, 2001
54.
Charushinx V.N., Mochulskaya N.N., Andreiko A.A., Kodess M.I., Chupakhin O.N.
Mendeleev Communications, 2002
55.
Aminovinyl ketones and aminovinyl esters as CCN building blocks for the synthesis of 1H-pyrrolo[3,2-e]1,2,4-triazines
Charushin V.N., Mochulskaya N.N., Andreiko A.A., Filyakova V.I., Kodess M.I., Chupakhin O.N.
Tetrahedron Letters, 2003
56.
Annelation of the thiazole ring to 1,2,4-triazines by tandem AN—ANor SNH—SNHreactions
Mochul"skaya N.N., Andreiko A.A., Kodess M.I., Vasil"eva E.B., Filyakova V.I., Gubaidullin A.T., Litvinov I.A., Sinyashin O.G., Aleksandrov G.G., Charushin V.N.
Russian Chemical Bulletin, 2004
57.
Krayushkin M.M., Yarovenko V.N., Sedishev I.P., Andreiko A.A., Mochulskaya N.N., Charushin V.N.
Mendeleev Communications, 2005
59.
Ponizovsky M.G., Boguslavsky A.M., Kodess M.I., Charushin V.N., Chupakhin O.N.
Mendeleev Communications, 2002
60.
New method for the annelation of the pyridine fragment to azines
Charushin V.N., Boguslavsky A.M., Ponizovsky M.G., Kodess M.I., Chekhlov A.N., Mkoyan S.G., Aldoshin S.M.
Russian Chemical Bulletin, 2004
62.
Kozhevnikov D.N., Kozhevnikov V.N., Nikitina T.V., Rusinov V.L., Chupakhin O.N., Neunhoeffer H.
Mendeleev Communications, 2002
63.
A new route to 6,6″-dicyano-2,2′:6′,2″-terpyridines and their complexes with Ni(II)
Kozhevnikov D.N., Kozhevnikov V.N., Nikitina T.V., Rusinov V.L., Chupakhin O.N., Eremenko I.L., Aleksandrov G.G.
Tetrahedron Letters, 2002
64.
A Versatile Strategy for the Synthesis of Functionalized 2,2‘-Bi- and 2,2‘:6‘,2‘ ‘-Terpyridines via Their 1,2,4-Triazine Analogues
Kozhevnikov V.N., Kozhevnikov D.N., Nikitina T.V., Rusinov V.L., Chupakhin O.N., Zabel M., König B.
Journal of Organic Chemistry, 2003
65.
Synthesis of Functionalized Fluorescent Europium(III) Terpyridyl Chelates
König B., Kozhevnikov V.N., Kozhevnikov D.N., Rusinov V.L., Chupakhin O.N.
Synthesis, 2003
66.
Kozhevnikov V.N., Kozhevnikov D.N., Shabunina O.V., Rusinov V.L., Chupakhin O.N., Zabel M., König B.
Mendeleev Communications, 2005
67.
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