Home / Articles / Advances in the synthesis of 4-aryl- and 4-hetarylpyridines

Advances in the synthesis of 4-aryl- and 4-hetarylpyridines

Sergei Panteleimonovich Gromov
, 
Marina Viktorovna Fomina 1
Marina Viktorovna Fomina
1 Photochemistry Centre, Russian Academy of Sciences, Moscow
Published 30 November 2007
7
Share
Cite this
GOST
 | 
Cite this
GOST
Gromov S. P., Fomina M. V. Advances in the synthesis of 4-aryl- and 4-hetarylpyridines // Russian Chemical Reviews. 2008. Vol. 77. No. 12. pp. 1055-1077.
GOST all authors (up to 50)
Gromov S. P., Fomina M. V. Advances in the synthesis of 4-aryl- and 4-hetarylpyridines // Russian Chemical Reviews. 2008. Vol. 77. No. 12. pp. 1055-1077.
RIS
 | 
Cite this
RIS
TY - JOUR
DO - 10.1070/RC2008v077n12ABEH003783
UR - https://rcr.colab.ws/publications/10.1070/RC2008v077n12ABEH003783
TI - Advances in the synthesis of 4-aryl- and 4-hetarylpyridines
T2 - Russian Chemical Reviews
AU - Gromov, Sergei Panteleimonovich
AU - Fomina, Marina Viktorovna
PY - 2008
DA - 2007/11/30
PB - ANO Editorial Board of the journal Uspekhi Khimii
SP - 1055-1077
IS - 12
VL - 77
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors)
@article{2008_Gromov,
author = {Sergei Panteleimonovich Gromov and Marina Viktorovna Fomina},
title = {Advances in the synthesis of 4-aryl- and 4-hetarylpyridines},
journal = {Russian Chemical Reviews},
year = {2008},
volume = {77},
publisher = {ANO Editorial Board of the journal Uspekhi Khimii},
month = {Nov},
url = {https://rcr.colab.ws/publications/10.1070/RC2008v077n12ABEH003783},
number = {12},
pages = {1055--1077},
doi = {10.1070/RC2008v077n12ABEH003783}
}
MLA
Cite this
MLA
Gromov, Sergei Panteleimonovich, and Marina Viktorovna Fomina. “Advances in the synthesis of 4-aryl- and 4-hetarylpyridines.” Russian Chemical Reviews, vol. 77, no. 12, Nov. 2008, pp. 1055-1077. https://rcr.colab.ws/publications/10.1070/RC2008v077n12ABEH003783.
Views / Visits / Downloads
13 / 13 / 4

Abstract

Information on the methods of synthesis of 4-aryl- or 4-hetaryl-substituted pyridines developed in the recent years is discussed and generalised. Examples of the practical use of 4-(het)arylpyridine derivatives are given.

References

1.
1
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1948
6.
10.1021/ic010338+
7.
Novel ruthenium sensitizers containing functionalized hybrid tetradentate ligands: synthesis, characterization, and INDO/S analysis.
Renouard T., Fallahpour R.-., Nazeeruddin M.K., Humphry-Baker R., Gorelsky S.I., Lever A.B., Grätzel M.
Inorganic Chemistry , 2002
8.
Electron donor-acceptor dyads based on ruthenium(II) bipyridine and terpyridine complexes bound to naphthalenediimide.
Johansson O., Borgström M., Lomoth R., Palmblad M., Bergquist J., Hammarström L., Sun L., Åkermark B.
Inorganic Chemistry , 2003
10.
A Europium(III) Complex as an Efficient Singlet Oxygen Luminescence Probe
Song B., Wang G., Tan M., Yuan J.
Journal of the American Chemical Society , 2006
11.
Luminescent complexes of iridium(III) containing N/\C/\N-coordinating terdentate ligands.
Wilkinson A.J., Puschmann H., Howard J.A., Foster C.E., Williams J.A.
Inorganic Chemistry , 2006
14.
Role of chelate substituents and cis σ-effect on the rate of ligand substitution at Pt(N–N–N) and Pt(N–N–C) centres
Jaganyi D., Reddy D., Gertenbach J.A., Hofmann A., van Eldik R.
Dalton Transactions , 2004
15.
Helical polymeric network of [ZnCl2(4′-aryl-4,2′-6′,4″-terpyridine)]n
16.
Right-Handed Helical Structure of Expanded Oligo(l-leucine) Containing [Ru(terpyridine)2]2+ Moieties
Okamura T., Iwamura T., Seno S., Yamamoto H., Ueyama N.
Journal of the American Chemical Society , 2004
18.
18
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1951
20.
Luminescent poly(phenylene vinylene) derivatives withm-terphenyl or 2,6-diphenylpyridine kinked segments along the main chain: Synthesis, characterization, and stimulated emission
Karastatiris P., Mikroyannidis J.A., Spiliopoulos I.K., Fakis M., Persephonis P.
Journal of Polymer Science, Part A: Polymer Chemistry , 2004
21.
21
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1958
22.
22
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1958
23.
Photoluminescence and electroluminescence of a series of terbium complexes
Gao X., Cao H., Huang C., Umitani S., Chen G., Jiang P.
Synthetic Metals , 1999
24.
Bright red light‐emitting organic electroluminescent devices based on a novel thiophene‐containing europium complex as an emitting layer
Okada K., Wang Y., Chen T., Kitamura M., Nakaya T., Inoue H.
Journal of Materials Chemistry A , 1999
26.
Pyridine Derivatives: Structure-Activity Relationships Causing Parkinsonism-Like Symptoms
Bachurin S.O., Tkachenko S.E., Lermontova N.N.
Reviews of Environmental Contamination and Toxicology , 1991
27.
Structure-neurotoxicity trends of analogues of 1-methyl-4-phenylpyridinium (MPP+), the cytotoxic metabolite of the dopaminergic neurotoxin MPTP
28.
10.1002/(SICI)1522-7146(1996)11:1<33::AID-JBT5>3.0.CO;2-W
30.
30
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1954
31.
31
A. A. Krasnovskii
Biokhimiya , 1960
32.
32
A. A. Krasnovskii
Dokl. Akad. Nauk SSSR , 1952
33.
Anti-inflammatory, analgesic and antipyretic 4,6-disubstituted 3-cyano-2-aminopyridines
Manna F., Chimenti F., Bolasco A., Bizzarri B., Filippelli W., Filippelli A., Gagliardi L.
European Journal of Medicinal Chemistry , 1999
34.
Crystal Structure of 1-Ethyl-1,4-dihydro-4-oxo-7-(4-pyridyl)-3-quinoline Carboxylic Acid (Rosoxacin).
Hernandez-Quiroz T., Hernández-Ortega S., Soriano-García M.
Analytical Sciences , 1998
35.
4-Phenylpyridine glucagon receptor antagonists: synthetic approaches to the sterically hindered chiral hydroxy group
36.
Integration of optimized substituent patterns to produce highly potent 4-aryl-pyridine glucagon receptor antagonists.
Ladouceur G.H., Cook J.H., Hertzog D.L., Jones J.H., Hundertmark T., Korpusik M., Lease T.G., Livingston J.N., MacDougall M.L., Osterhout M.H., Phelan K., Romero R.H., Schoen W.R., Shao C., Smith R.A., et. al.
Bioorganic and Medicinal Chemistry Letters , 2002
37.
Optimization of the 4-aryl group of 4-aryl-pyridine glucagon antagonists: development of an efficient, alternative synthesis.
Smith R.A., Hertzog D.L., Osterhout M.H., Ladouceur G.H., Korpusik M., Bobko M.A., Jones J.H., Phelan K., Romero R.H., Hundertmark T., MacDougall M.L., Livingston J.N., Schoen W.R.
Bioorganic and Medicinal Chemistry Letters , 2002
38.
38
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1956
39.
39
V. F. Gachkovskii
Biofizika , 1959
40.
Paraquat-Induced Cell Death in PC12 Cells
Yang W., Sun A.Y.
Neurochemical Research , 1998
43.
Solid-Phase Synthesis of 2,4,6-Trisubstituted Pyridines
Chiu C., Tang Z., Ellingboe J.W.
Journal of Combinatorial Chemistry , 1998
45.
45
W. Hendrich
Roczniki Chemii , 1958
46.
46
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1955
49.
49
A. A. Krasnovskii
Biofizika , 1958
51.
Ditopic N-Crowned 4-(p-Aminophenyl)-2,6-diphenylpyridines:  Implications of Macrocycle Topology on the Spectroscopic Properties, Cation Complexation, and Differential Anion Responses
García-Acosta B., Martínez-Máñez R., Sancenón F., Soto J., Rurack K., Spieles M., García-Breijo E., Gil L.
Inorganic Chemistry , 2007
52.
52
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1957
53.
53
D. Porretand E. Rabinowitch
Nature , 1937
54.
Synthesis and characterization of new polybenzimidazopyrrolones derived from pyridine-bridged aromatic tetraamines and dianhydrides
Liu J., Wang L., Yang H., Li H., Li Y., Fan L., Yang S.
Journal of Polymer Science, Part A: Polymer Chemistry , 2004
55.
Diverse Synthesis of Novel Bisterpyridines via Suzuki-Type Cross-Coupling
57.
A Green and Straightforward Synthesis of 4′-Substituted Terpyridines
Schubert U., Winter A., van den Berg A., Hoogenboom R., Kickelbick G.
Synthesis , 2006
61.
Research and Development of an Efficient Process for the Construction of the 2,4,5-Substituted Pyridines of NK-1 Receptor Antagonists
Harrington P.J., Johnston D., Moorlag H., Wong J., Hodges L.M., Harris L., McEwen G.K., Smallwood B.
Organic Process Research and Development , 2006
62.
A new and convenient one-pot solid supported synthesis of 2,4,6-triarylpyridines
Kumar A., Koul S., Razdan T.K., Kapoor K.K.
Tetrahedron Letters , 2006
64.
Synthesis of aromatic heterocycles
Gilchrist T.L.
Journal of the Chemical Society Perkin Transactions 1 , 2001
66.
66
V. B. Evstigneev
Dokl. Akad. Nauk SSSR , 1950
67.
Self-Assembly of Twisted Bridging Ligands to Helical Coordination Polymers
Kimura M., Sano M., Muto T., Hanabusa K., Shirai H., Kobayashi N.
Macromolecules , 1999
70.
70
N. Bubnov
Biofizika , 1960
72.
72
A. F. Lukovnikov
"Starenie i Stabilizatsiya Polimerov" (Aging arid Stabilisation of Polymers) , 1963
73.
Synthesis of 4,4′-(1,4-Phenylene)di-pyridine and-pyrimidine Derivatives†
Shaker R.M., Abdel-Latif F.F.
Journal of Chemical Research , 1997
74.
10.1021/ol052994+
75.
One-Step Synthesis of Heterocyclic Privileged Medicinal Scaffolds by a Multicomponent Reaction of Malononitrile with Aldehydes and Thiols
Evdokimov N.M., Kireev A.S., Yakovenko A.A., Antipin M.Y., Magedov I.V., Kornienko A.
Journal of Organic Chemistry , 2007
78.
Soldatenkov Anatoly Timofeevich, Polyanskii Kirill Borisovich, Shereshovets Valerii Vladimirovich, Soldatova Svetlana Aleksandrovna, Sergeeva Nataliya Dmitrievna, Kolyadina Nadezhda Mikhailovna, Lobanov Nikolai Nikolaevich
Mendeleev Communications , 2001
79.
Synthesis and reactions of 2-amino-6-(3-methyl-5-oxo-1-phenyl-2-pyrazolin-4-yl)-4-phenylpyridine-3-carbonitrile
Ahmed R.A., Kandeel M.M., Abbady M.S., Youssef M.S.
Journal of Heterocyclic Chemistry , 2002
80.
Preparation of 2,6-Dimethyl-4-arylpyridine- 3,5-dicarbonitrile:  A Paired Electrosynthesis
Batanero B., Barba F., Martín A.
Journal of Organic Chemistry , 2002
81.
Vilsmeier–Haack reaction of tertiary alcohols: formation of functionalised pyridines and naphthyridines
Thomas A.D., Asokan C.V.
Journal of the Chemical Society Perkin Transactions 1 , 2001
83.
Cycloadditions of NS functions to cyclopentadienones
Chabane H., Meth-Cohn O., Rees C.W., White A.J., Williams D.J.
Tetrahedron Letters , 2003
86.
One-Pot Synthesis of Metalated Pyridines from Two Acetylenes, a Nitrile, and a Titanium(II) Alkoxide
Tanaka R., Yuza A., Watai Y., Suzuki D., Takayama Y., Sato F., Urabe H.
Journal of the American Chemical Society , 2005
97.
Tandem Michael Addition/Amino-Nitrile Cyclization from 2-Formyl-1,4-DHP in the Synthesis of Novel Dihydroindolizine-Based Compounds
Marchalín Š., Baumlová B., Baran P., Oulyadi H., Daïch A.
Journal of Organic Chemistry , 2006
98.
A Convenient Synthesis of 2,4'-Bipyridine
Shiao M., Tarng K.
Heterocycles , 1990
99.
A Convenient Synthesis of Five-membered Heteroaryl-substituted Pyridines
101.
Magnetic and structural transitions in layered iron arsenide systems: AFe2As2 versus RFeAsO
Krellner C., Caroca-Canales N., Jesche A., Rosner H., Ormeci A., Geibel C.
Physical Review B , 2008
102.
102
F. Fichter
Helv. Chim. Acta , 1922
103.
Soldatenkov Anatoly Timofeevich, Polyanskii Kirill Borisovich, Shereshovets Valerii Vladimirovich, Soldatova Svetlana Aleksandrovna, Sergeeva Nataliya Dmitrievna, Kolyadina Nadezhda Mikhailovna, Lobanov Nikolai Nikolaevich
Mendeleev Communications , 2001
104.
104
O. P. Osipova
Dokl. Akad. Nauk SSSR , 1950
105.
Selective Reductions of 1-Methyl-4-phenyl-2-pyridone
Mabic S., Castagnoli N.
Journal of Organic Chemistry , 1996
106.
Synthesis of Biaryls via Intermolecular Radical Addition of Heteroaryl and Aryl Bromides onto Arenes
Martínez-Barrasa V., García de Viedma A., Burgos C., Alvarez-Builla J.
Organic Letters , 2000
107.
Delocalized Nitrogen Carbanions in SRN1 Reactions
Chahma M., Combellas C., Thiebault A.
Journal of Organic Chemistry , 1995
108.
Preparation of extended di(4-pyridyl)thiophene oligomers
Albers W.M., Canters G.W., Reedijk J.
Tetrahedron , 1995
110.
Syntheses and photophysical properties of some 4-arylpyridinium salts
Kelley C.J., Ansu K., Budisusetyo W., Ghiorghis A., Qin Y., Kauffman J.M.
Journal of Heterocyclic Chemistry , 2001
115.
Pyridinylzinc halides by oxidative addition of active zinc with halopyridines
Sakamoto T., Kondo Y., Murata N., Yamanaka H.
Tetrahedron Letters , 1992
122.
Highly Active Two-Photon Dyes:  Design, Synthesis, and Characterization toward Application
Reinhardt B.A., Brott L.L., Clarson S.J., Dillard A.G., Bhatt J.C., Kannan R., Yuan L., He G.S., Prasad P.N.
Chemistry of Materials , 1998
124.
Synthesis and cytotoxicity of 6,11-Dihydro-pyrido- and 6,11-Dihydro-benzo[2,3-b]phenazine-6,11-dione derivatives
Kim Y., Park S., Lee H., Suh M., Schollmeyer D., Lee C.
Bioorganic and Medicinal Chemistry , 2003
125.
125
K. A. Andrianov
Vysokomol. Soed. , 1960
127.
A novel synthesis of 4-aryl- and 4-heteroarylpyridines via diethyl(4-pyridyl)borane.
ISHIKURA M., OHTA T., TERASHIMA M.
Chemical and Pharmaceutical Bulletin , 2011
129.
Fluorescence of amphiphilic hemicyanine dyes without free double bonds
Ephardt H., Fromherz P.
The Journal of Physical Chemistry , 1993
131.
Palladium-catalyzed alkylations in aqueous media
Casalnuovo A.L., Calabrese J.C.
Journal of the American Chemical Society , 1990
136.
Synthesis of Anthryl-Substituted Bithienylpyridines and their N-Methylpyridinium Salts
Effenberger F., Endtner J.M., Miehlich B., Münter J.S., Vollmer M.S.
Synthesis , 2000
137.
137
S. R. Rafikov
Zh. Obshch. Khim. , 1944
138.
Perkin communications. Synthesis of 3-amino-4-phenylpyridines: a novel strategy for the preparation ofCDring models of streptonigrin
Marsais F., Rovera J., Turck A., Godard A., Quéguiner G.
Journal of the Chemical Society Perkin Transactions 1 , 1990
140.
Synthesis of poly(pyridylthioether) dendrimers incorporating a Fe2(CO)6 cluster core
Chessa G., Canovese L., Visentin F., Santo C., Seraglia R.
Tetrahedron , 2005
142.
An efficient synthesis of a highly functionalized 4-arylpiperidine
Boice G.N., Savarin C.G., Murry J.A., Conrad K., Matty L., Corley E.G., Smitrovich J.H., Hughes D.
Tetrahedron , 2004
143.
Boronic Acid-Based Bipyridinium Salts as Tunable Receptors for Monosaccharides and α-Hydroxycarboxylates
Gamsey S., Miller A., Olmstead M.M., Beavers C.M., Hirayama L.C., Pradhan S., Wessling R.A., Singaram B.
Journal of the American Chemical Society , 2007
144.
Stereoselective association of binuclear metallacycles in coordination polymers.
Khlobystov A.N., Brett M.T., Blake A.J., Champness N.R., Gill P.M., O'Neill D.P., Teat S.J., Wilson C., Schröder M.
Journal of the American Chemical Society , 2003
145.
Six-Step Synthesis of (S)-Brevicolline from (S)-Nicotine
Wagner F.F., Comins D.L.
Organic Letters , 2006
146.
An Efficient Two-Step Total Synthesis of the Quaterpyridine Nemertelline
Bouillon A., Voisin A.S., Robic A., Lancelot J., Collot V., Rault S.
Journal of Organic Chemistry , 2003
150.
Synthesis and Spectral Properties of 5,5′-Di(4-pyridyl)-2,2′-bithienyl as a New Fluorescent Compound
Nakajima R., Iida H., Hara T.
Bulletin of the Chemical Society of Japan , 1990
152.
Palladium-Catalyzed Tetrakis(dimethylamino)ethylene-Promoted Reductive Coupling of Aryl Halides
155.
Copper fluorapatite catalyzed N-arylation of heterocycles with bromo and iodoarenes
Lakshmi Kantam M., Venkanna G.T., Sridhar C., Shiva Kumar K.B.
Tetrahedron Letters , 2006
158.
From Five- to Six-Membered Rings:  3,4-Diarylquinolinone as Lead for Novel p38MAP Kinase Inhibitors
Peifer C., Kinkel K., Abadleh M., Schollmeyer D., Laufer S.
Journal of Medicinal Chemistry , 2007
159.
159
J. Tafel
Z. Elektrochem. , 1911
160.
160
1912
161.
161
Friedl.
162.
10.1002/1099-0690(200212)2002:24<4123::AID-EJOC4123>3.0.CO;2-M
163.
163
Friedl.
164.
Synthesis and Thermal Stability of S-Trimethylsilyl-S′-ethyl(diethylamido)trithiophosphate
Nizamov I.S., Abalonin B.E., Bol'shakova O.V., Nizamov I.D., Sergeenko G.G., Al'metkina L.A., Krivolapov D.B., Batyeva E.S., Litvinov I.A.
Russian Journal of Organic Chemistry , 2005
165.
165
Friedl.
166.
166
1917