Home / Publications / Rational synthetic methods in creating promising (hetero)aromatic molecules and materials

Rational synthetic methods in creating promising (hetero)aromatic molecules and materials

Grigory Vasil'evich Zyryanov 1, 2
Grigory Vasil'evich Zyryanov
Dmitrii Sergeevich Kopchuk 1, 2
Dmitrii Sergeevich Kopchuk
Igor Sergeevich Kovalev 1
Igor Sergeevich Kovalev
Sougata Santra 1
Sougata Santra
Matiur Rahman 1
Matiur Rahman
Albert Faridovich Khasanov 1, 2
Albert Faridovich Khasanov
Alexey P Krinochkin 1, 2
Alexey P Krinochkin
Olga Sergeevna Taniya 1, 2
Olga Sergeevna Taniya
Oleg Nikolaevich Chupakhin 1, 2
Oleg Nikolaevich Chupakhin
Valery Nikolaevich Charushin
Published 2020-08-31
Focus articleVolume 30, Issue 5, 537-554
17
Share
Cite this
GOST
 | 
Cite this
GOST Copy
Zyryanov G. V. et al. Rational synthetic methods in creating promising (hetero)aromatic molecules and materials // Mendeleev Communications. 2020. Vol. 30. No. 5. pp. 537-554.
GOST all authors (up to 50) Copy
Zyryanov G. V., Kopchuk D. S., Kovalev I. S., Santra S., Rahman M., Khasanov A. F., Krinochkin A. P., Taniya O. S., Chupakhin O. N., Charushin V. N. Rational synthetic methods in creating promising (hetero)aromatic molecules and materials // Mendeleev Communications. 2020. Vol. 30. No. 5. pp. 537-554.
RIS
 | 
Cite this
RIS Copy
TY - JOUR
DO - 10.1016/j.mencom.2020.09.001
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2020.09.001
TI - Rational synthetic methods in creating promising (hetero)aromatic molecules and materials
T2 - Mendeleev Communications
AU - Zyryanov, Grigory Vasil'evich
AU - Kopchuk, Dmitrii Sergeevich
AU - Kovalev, Igor Sergeevich
AU - Santra, Sougata
AU - Rahman, Matiur
AU - Khasanov, Albert Faridovich
AU - Krinochkin, Alexey P
AU - Taniya, Olga Sergeevna
AU - Chupakhin, Oleg Nikolaevich
AU - Charushin, Valery Nikolaevich
PY - 2020
DA - 2020/08/31
PB - Mendeleev Communications
SP - 537-554
IS - 5
VL - 30
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors) Copy
@article{2020_Zyryanov,
author = {Grigory Vasil'evich Zyryanov and Dmitrii Sergeevich Kopchuk and Igor Sergeevich Kovalev and Sougata Santra and Matiur Rahman and Albert Faridovich Khasanov and Alexey P Krinochkin and Olga Sergeevna Taniya and Oleg Nikolaevich Chupakhin and Valery Nikolaevich Charushin},
title = {Rational synthetic methods in creating promising (hetero)aromatic molecules and materials},
journal = {Mendeleev Communications},
year = {2020},
volume = {30},
publisher = {Mendeleev Communications},
month = {Aug},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2020.09.001},
number = {5},
pages = {537--554},
doi = {10.1016/j.mencom.2020.09.001}
}
MLA
Cite this
MLA Copy
Zyryanov, Grigory Vasil'evich, et al. “Rational synthetic methods in creating promising (hetero)aromatic molecules and materials.” Mendeleev Communications, vol. 30, no. 5, Aug. 2020, pp. 537-554. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2020.09.001.
Views / Downloads
1 / 1

Keywords

(hetero)arenes
C–H functionalization
chemosensors
drug candidates
fluorophores
ligands
macrocycles
transition metal-free methods

Abstract

In this focus article, the recent syntheses of various (hetero)aromatic/macrocyclic molecules/scaffolds such as (thia)calixarenes, iptycenes, [poly](aza)arenes, 2,2′bipyridines, 1,2,4triazines, (ox)azoles and aziri(di)nes are reviewed. The employed rational synthetic schemes and green chemistry principles such as solventfree reactions, reactions in ionic liquids, arynemediated reactions, domino and multicomponent reactions, sono, photoand mechanoactivated processes, and direct C–H functionalization are described. The obtained compounds exhibited promising photophysical and coordination properties, intriguing supramolecular properties as well as biological activities. The possible application of these compounds as fluorophores, luminophores, organic phosphors, chemosensors, ligands and drug candidates is discussed.

References

1.
Picking a winner
Sheldon R.
Nature, 1999
2.
Solvent-Free Organic Synthesis
Tanaka K., Toda F.
Chemical Reviews, 2000
3.
10.1016/j.mencom.2020.09.001_bib0015
Green Chemistry Education: Changing the Course of Chemistry, 2009
4.
Pot economy and one-pot synthesis
Hayashi Y.
Chemical Science, 2016
5.
10.1016/j.mencom.2020.09.001_bib0025
Green Chemistry and Catalysis, 2007
7.
Green Chemistry Metrics with Special Reference to Green Analytical Chemistry
Tobiszewski M., Marć M., Gałuszka A., Namieśnik J.
Molecules, 2015
8.
A decade update on solvent and catalyst-free neat organic reactions: a step forward towards sustainability
Sarkar A., Santra S., Kundu S.K., Hajra A., Zyryanov G.V., Chupakhin O.N., Charushin V.N., Majee A.
Green Chemistry, 2016
10.
Solvent-free and catalysts-free chemistry: a benign pathway to sustainability.
Gawande M.B., Bonifácio V.D., Luque R., Branco P.S., Varma R.S.
ChemSusChem, 2013
15.
10.1016/j.mencom.2020.09.001_bib0075
Steed
Supramolecular Chemistry, 2001
16.
Molecular Properties That Influence the Oral Bioavailability of Drug Candidates
Veber D.F., Johnson S.R., Cheng H., Smith B.R., Ward K.W., Kopple K.D.
Journal of Medicinal Chemistry, 2002
17.
Testing the Conformational Hypothesis of Passive Membrane Permeability Using Synthetic Cyclic Peptide Diastereomers
Rezai T., Yu B., Millhauser G.L., Jacobson M.P., Lokey R.S.
Journal of the American Chemical Society, 2006
18.
Efficient inhibition of human papillomavirus 16 L1 pentamer formation by a carboxylatopillarene and a p-sulfonatocalixarene.
Zheng D., Fu D., Wu Y., Sun Y., Tan L., Zhou T., Ma S., Zha X., Yang Y.
Chemical Communications, 2014
19.
Cyclic polyethers and their complexes with metal salts
Pedersen C.J.
Journal of the American Chemical Society, 1967
20.
Cyclic polyethers and their complexes with metal salts
Pedersen C.J.
Journal of the American Chemical Society, 1967
21.
Calixarenes for metal cations extraction
Dumazet-Bonnamour I., Halouani H., Oueslati F., Lamartine R.
Comptes Rendus Chimie, 2005
23.
Yakimova L.S., Padnya P.L., Kunafina A.F., Nugmanova A.R., Stoikov I.I.
Mendeleev Communications, 2019
24.
Inclusion of Organic Cations by Calix[n]arenes
Abraham W.
Journal of Inclusion Phenomena and Macrocyclic Chemistry, 2002
25.
Mostovaya O.A., Valiullina Y.A., Chan C.T., Potrekeeva O.S., Padnya P.L., Zuev Y.F., Stoikov I.I.
Mendeleev Communications, 2019
26.
Association and orientation of C70 on complexation with calix[5]arene
Atwood J.L., Barbour L.J., Heaven M.W., Raston C.L.
Chemical Communications, 2003
27.
Thiacalixarenes
Morohashi N., Narumi F., Iki N., Hattori T., Miyano S.
Chemical Reviews, 2006
30.
Shell closure of two cavitands forms carcerand complexes with components of the medium as permanent guests
Cram D.J., Karbach S., Kim Y.H., Baczynskyj L., Kallemeyn G.W.
Journal of the American Chemical Society, 1985
31.
Recent Highlights in Hemicarcerand Chemistry
Warmuth R., Yoon J.
Accounts of Chemical Research, 2001
32.
para-Bridged symmetrical pillar[5]arenes: their Lewis acid catalyzed synthesis and host-guest property.
Ogoshi T., Kanai S., Fujinami S., Yamagishi T., Nakamoto Y.
Journal of the American Chemical Society, 2008
33.
Pillararenes, a new class of macrocycles for supramolecular chemistry.
Xue M., Yang Y., Chi X., Zhang Z., Huang F.
Accounts of Chemical Research, 2012
34.
Synthesis and host-guest properties of pillar[6]arenes
Tao H., Cao D., Liu L., Kou Y., Wang L., Meier H.
Science China Chemistry, 2011
35.
The template effect of solvents on high yield synthesis, co-cyclization of pillar[6]arenes and interconversion between pillar[5]- and pillar[6]arenes
Ogoshi T., Ueshima N., Akutsu T., Yamafuji D., Furuta T., Sakakibara F., Yamagishi T.
Chemical Communications, 2014
38.
Counter-ion and solvent effects on the acidity of calix[4]arene and para-tert-butylcalix[6]arene
Miñambres G.G., Jaques T.S., Veglia A.V., Lazzarotto M., Nachtigall F.F.
Journal of Inclusion Phenomena and Macrocyclic Chemistry, 2014
39.
Solvent-free synthesis of pillar[6]arenes
Santra S., Kopchuk D.S., Kovalev I.S., Zyryanov G.V., Majee A., Charushin V.N., Chupakhin O.N.
Green Chemistry, 2016
40.
Kovalev I.S., Rahman M., Sadieva L.K., Pavlyuk D.E., Giri K., Santra S., Kopchuk D.S., Zyryanov G.V., Majee A., Chupakhin O.N., Charushin V.N.
Arkivoc, 2017
41.
Synthesis and structural exploration of disulfide bridged [2n] pillararene-like molecules
Sonawane M.P., Jacobs J., Thomas J., Van Meervelt L., Dehaen W.
Chemical Communications, 2013
42.
Dynamic combinatorial libraries of metalloporphyrins: templated amplification of disulfide-linked oligomers
Kieran A.L., Bond A.D., Belenguer A.M., Sanders J.K.
Chemical Communications, 2003
43.
Dynamic Combinatorial Libraries of Macrocyclic Disulfides in Water
Otto S., Furlan R.L., Sanders J.K.
Journal of the American Chemical Society, 2000
45.
Mechanosensitive Self-Replication Driven by Self-Organization
Carnall J.M., Waudby C.A., Belenguer A.M., Stuart M.C., Peyralans J.J., Otto S.
Science, 2010
46.
Template-directed synthesis of multi-component organic cages in water
Stefankiewicz A.R., Sambrook M.R., Sanders J.K.
Chemical Science, 2012
47.
A. F. Khasanov, I.S. Kovalev, D.S. Kopchuk, S. Santra, M. Rahman, S.S. Rybakova, G.V. Zyryanov, O. N. Chupakhin, AIP Conf. Proc., 2020, in press.
49.
10.1016/j.mencom.2020.09.001_bib0230
Bolz
The Counterterrorism Handbook: Tactics, Procedures, and Techniques, 2012
50.
Chemosensors for detection of nitroaromatic compounds (explosives)
Zyryanov G.V., Kopchuk D.S., Kovalev I.S., Nosova E.V., Rusinov V.L., Chupakhin O.N.
Russian Chemical Reviews, 2014
52.
Triptycene1 (9,10-o-Benzenoanthracene)
Bartlett P.D., Ryan M.J., Cohen S.G.
Journal of the American Chemical Society, 1942
53.
10.1016/j.mencom.2020.09.001_bib0250
Chen
Iptycenes Chemistry: From Synthesis to Applications, 2012
54.
Iptycenes in the Design of High Performance Polymers
Swager T.M.
Accounts of Chemical Research, 2008
55.
Finely Tuning the Free Volume Architecture in Iptycene-Containing Polyimides for Highly Selective and Fast Hydrogen Transport
Luo S., Wiegand J.R., Kazanowska B., Doherty C.M., Konstas K., Hill A.J., Guo R.
Macromolecules, 2016
56.
Synthesis and characterization of triptycene-based polyimides with tunable high fractional free volume for gas separation membranes
Wiegand J.R., Smith Z.P., Liu Q., Patterson C.T., Freeman B.D., Guo R.
Journal of Materials Chemistry A, 2014
59.
High Performance Polyimide with High Internal Free Volume Elements
Cho Y.J., Park H.B.
Macromolecular Rapid Communications, 2011
61.
Porous Shape Persistent Fluorescent Polymer Films:  An Approach to TNT Sensory Materials
62.
Fluorescent Porous Polymer Films as TNT Chemosensors:  Electronic and Structural Effects
63.
Acylarylnitrosamines. Part III. Decomposition of 2,5-di-(N-nitrosoacetamido)-1,4-di-t-butylbenzene and related compounds
Cadogan J.I., Harger M.J., Sharp J.T.
Journal of the Chemical Society B Physical Organic, 1971
64.
Generalization of the triptycene concept. Use of diaryne equivalents in the synthesis of iptycenes
65.
Simple Molecule-Based Fluorescent Sensors for Vapor Detection of TNT
Zyryanov G.V., Palacios M.A., Anzenbacher P.
Organic Letters, 2008
66.
Host–Guest Complexes of Pentiptycene Receptors Display Edge-to-Face Interaction
Mosca L., Koutník P., Lynch V.M., Zyryanov G.V., Esipenko N.A., Anzenbacher P.
Crystal Growth and Design, 2012
67.
Iptycene-based fluorescent sensors for nitroaromatics and TNT.
Anzenbacher P., Mosca L., Palacios M.A., Zyryanov G.V., Koutnik P.
Chemistry - A European Journal, 2012
68.
Extended cavity pyrene-based iptycenes for the turn-off fluorescence detection of RDX and common nitroaromatic explosives
Khasanov A.F., Kopchuk D.S., Kovalev I.S., Taniya O.S., Giri K., Slepukhin P.A., Santra S., Rahman M., Majee A., Charushin V.N., Chupakhin O.N.
New Journal of Chemistry, 2017
69.
10.1016/j.mencom.2020.09.001_bib0330
Stenersen
Chemical Pesticides Mode of Action and Toxicology, 2004
71.
10.1002/1521-3773(20010601)40:11<2104::AID-ANIE2104>3.0.CO;2-#
72.
A Pattern Recognition Based Fluorescence Quenching Assay for the Detection and Identification of Nitrated Explosive Analytes
73.
A water-soluble cationic oligopyrene derivative: Spectroscopic studies and sensing applications
Chen Y., Bai H., Chen Q., Li C., Shi G.
Sensors and Actuators, B: Chemical, 2009
75.
Simple Pyrene Derivatives as Fluorescence Sensors for TNT and RDX in Micelles
Hong J., Choi J., Cho D.
Bulletin of the Korean Chemical Society, 2014
76.
Fluorescent Detection of 2,4-DNT and 2,4,6-TNT in Aqueous Media by Using Simple Water-Soluble Pyrene Derivatives
Kovalev I.S., Taniya O.S., Slovesnova N.V., Kim G.A., Santra S., Zyryanov G.V., Kopchuk D.S., Majee A., Charushin V.N., Chupakhin O.N.
Chemistry - An Asian Journal, 2016
77.
1-Hydroxypyrene-based micelle-forming sensors for the visual detection of RDX/TNG/PETN-based bomb plots in water
Kovalev I.S., Taniya O.S., Kopchuk D.S., Giri K., Mukherjee A., Santra S., Majee A., Rahman M., Zyryanov G.V., Bakulev V.A., Chupakhin O.N.
New Journal of Chemistry, 2018
78.
10.1016/j.mencom.2020.09.001_bib0375
Lakowicz
Principles of Fluorescence Spectroscopy, 2006
80.
10.1016/j.mencom.2020.09.001_bib0385
Marshall
Clinical Chemistry, 2004
81.
10.1016/j.mencom.2020.09.001_bib0390
Human Physiology, 1989
82.
Rational Design of a Fluorescence-Turn-On Sensor Array for Phosphates in Blood Serum
Zyryanov G., Palacios M., Anzenbacher P.
Angewandte Chemie - International Edition, 2007
83.
First supramolecular sensors for phosphonate anions
Esipenko N.A., Koutnik P., Minami T., Mosca L., Lynch V.M., Zyryanov G.V., Anzenbacher P.
Chemical Science, 2013
84.
Organic host materials for phosphorescent organic light-emitting diodes.
85.
Solution processable small molecules for organic light-emitting diodes
Duan L., Hou L., Lee T., Qiao J., Zhang D., Dong G., Wang L., Qiu Y.
Journal of Materials Chemistry A, 2010
86.
10.1016/j.mencom.2020.09.001_bib0415
Organic Light-Emitting Materials and Devices, 2015
88.
Organic materials for electronic and optoelectronic devices
Shirota Y.
Journal of Materials Chemistry A, 2000
89.
Novel Carbazole/Fluorene Hybrids:  Host Materials for Blue Phosphorescent OLEDs
Shih P., Chiang C., Dixit A.K., Chen C., Yuan M., Lee R., Chen C., Diau E.W., Shu C.
Organic Letters, 2006
93.
Organocatalysis in cross-coupling: DMEDA-catalyzed direct C-H arylation of unactivated benzene.
Liu W., Cao H., Zhang H., Zhang H., Chung K.H., He C., Wang H., Kwong F.Y., Lei A.
Journal of the American Chemical Society, 2010
94.
tert-Butoxide-Mediated Arylation of Benzene with Aryl Halides in the Presence of a Catalytic 1,10-Phenanthroline Derivative
Shirakawa E., Itoh K., Higashino T., Hayashi T.
Journal of the American Chemical Society, 2010
95.
An efficient organocatalytic method for constructing biaryls through aromatic C–H activation
Sun C., Li H., Yu D., Yu M., Zhou X., Lu X., Huang K., Zheng S., Li B., Shi Z.
Nature Chemistry, 2010
96.
Simple CBP isomers with high triplet energies for highly efficient blue electrophosphorescence
Gong S., He X., Chen Y., Jiang Z., Zhong C., Ma D., Qin J., Yang C.
Journal of Materials Chemistry A, 2012
97.
Synthesis of symmetrical dicarbazole-biphenyls, components of phosphorescentorganic light-emitting diodes (PHOLEDs) using organocuprates
Zyryanov G.V., Kovalev I.S., Egorov I.N., Rusinov V.L., Chupakhin O.N.
Chemistry of Heterocyclic Compounds, 2011
98.
Synthesis of substituted 4,4´-dihalobiphenyls and their use for the preparation of isomeric bis(carbazolyl)biphenyls
Kovalev I.S., Pavlyuk D.E., Zaripov V.A., Zyryanov G.V., Kopchuk D.S., Rusinov V.L., Chupakhin O.N.
Russian Chemical Bulletin, 2015
101.
Correlation between the lowest triplet state energy level of the ligand and lanthanide(III) luminescence quantum yield
Latva M., Takalo H., Mukkala V., Matachescu C., Rodríguez-Ubis J.C., Kankare J.
Journal of Luminescence, 1997
102.
Farat O.K., Kharcheva A.V., Ioutsi V.A., Borisova N.E., Reshetova M.D., Patsaeva S.V.
Mendeleev Communications, 2019
103.
New Heteroaromatic Complexing Agents and Luminescence of Their Europium(III) and Terbium(III) Chelates
Mukkala V., Sund C., Kwiatkowski M., Pasanen P., Högberg M., Kankare J., Takalo H.
Helvetica Chimica Acta, 1992
105.
High Relaxivity Confined to a Small Molecular Space: A Metallostar-Based, Potential MRI Contrast Agent
Livramento J.B., Tóth É., Sour A., Borel A., Merbach A.E., Ruloff R.
Angewandte Chemie - International Edition, 2004
106.
Highly‐Luminescent DTTA‐Appended Water‐Soluble Lanthanide Complexes of 4‐(Het)aryl‐2,2′‐bipyridines: Synthesis and Photophysical Properties
Krinochkin A.P., Kopchuk D.S., Kim G.A., Ganebnykh I.N., Kovalev I.S., Santra S., Zyryanov G.V., Majee A., Rusinov V.L., Chupakhin O.N.
ChemistrySelect, 2019
107.
Synthesis and luminescence of new water-soluble lanthanide complexes of DTTA-containing 4-(4-methoxyphenyl)-2,2′-bipyridine
Krinochkin A.P., Kopchuk D.S., Kim G.A., Gorbunov E.B., Kovalev I.S., Santra S., Zyryanov G.V., Majee A., Rusinov V.L., Chupakhin O.N.
Inorganica Chimica Acta, 2018
108.
Direct Introduction of a Methyl Group at the C5‐Position of 1,2,4‐Triazines: Convenient Synthesis of 6‐Functionalized 5‐Aryl‐2,2′‐bipyridines
Krinochkin A.P., Kopchuk D.S., Kovalev I.S., Santra S., Zyryanov G.V., Majee A., Rusinov V.L., Chupakhin O.N.
ChemistrySelect, 2020
109.
Water-soluble luminescent lanthanide complexes based on C6-DTTA-appended 5-aryl-2,2′-bipyridines
Krinochkin A.P., Kopchuk D.S., Kim G.A., Shevyrin V.A., Santra S., Rahman M., Taniya O.S., Zyryanov G.V., Rusinov V.L., Chupakhin O.N.
Polyhedron, 2020
110.
One-Step Synthesis of 5-Methyl-1,2,4-triazines by the Transformation of Their 5-Phenacyl Derivatives
Krinochkin A.P., Kopchuk D.S., Kovalev I.S., Zyryanov G.V., Rusinov V.L., Chupakhin O.N.
Russian Journal of Organic Chemistry, 2019
111.
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
112.
DTTA-appended 6-phenyl- and 5,6-diphenyl-2,2′-bipyridines as new water soluble ligands for lanthanide cations
Krinochkin A.P., Kopchuk D.S., Kim G.A., Ganebnykh I.N., Kovalev I.S., Zyryanov G.V., Li F., Rusinov V.L., Chupakhin O.N.
Polyhedron, 2017
113.
Synthesis and photophysical studies of new organic-soluble lanthanide complexes of 4-(4-alkoxyphenyl)-2,2′-bipyridine-6-carboxylic acids
Krinochkin A.P., Kopchuk D.S., Kim G.A., Ganebnykh I.N., Kovalev I.S., Santra S., Majee A., Zyryanov G.V., Rusinov V.L., Chupakhin O.N.
Journal of Molecular Structure, 2019
114.
An efficient synthetic approach towards new 5,5’-diaryl-2,2’-bipyridine-based fluorophores
Krinochkin A.P., Kopchuk D.S., Chepchugov N.V., Kim G.A., Kovalev I.S., Rahman M., Zyryanov G.V., Majee A., Rusinov V.L., Chupakhin O.N.
Chinese Chemical Letters, 2017
115.
Synthesis and photophysics of new unsymmetrically substituted 5,5′-diaryl-2,2′-bypiridine-based “push-pull” fluorophores
Starnovskaya E.S., Kopchuk D.S., Khasanov A.F., Tanya O.S., Santra S., Giri K., Rahman M., Kovalev I.S., Zyryanov G.V., Majee A., Charushin V.N.
Dyes and Pigments, 2019
116.
The Extension of Conjugated System in Pyridyl-Substituted Monoazatriphenylenes for the Tuning of Photophysical Properties
Kopchuk D.S., Khasanov A.F., Kovalev I.S., Zyryanov G.V., Kim G.A., Nikonov I.L., Rusinov V.L., Chupakhin O.N.
Chemistry of Heterocyclic Compounds, 2014
117.
Synthesis and characterizations of new cadmium complexes based on poly(aza)arene-annelated 2,2′-bipyridines
Kopchuk D.S., Slepukhin P.A., Kovalev I.S., Khasanov A.F., Taniya O.S., Shabunina O.V., Zyryanov G.V., Rusinov V.L., Chupakhin O.N.
Polyhedron, 2016
118.
Preparation of Pyridyl-substituted Monoazatriphenylenes
Kopchuk D.S., Zyryanov G.V., Kovalev I.S., Khasanov A.F., Medvedevskikh A.S., Rusinov V.L., Chupakhin O.N.
Chemistry of Heterocyclic Compounds, 2013
119.
(Benzo[h])Quinolinyl-Substituted Monoazatriphenylenes: Synthesis and Photophysical Properties
Kopchuk D.S., Khasanov A.F., Kovalev I.S., Kim G.A., Nikonov I.L., Zyryanov G.V., Rusinov V.L., Chupakhin O.N.
Chemistry of Heterocyclic Compounds, 2014
120.
Synthesis and optical properties of new 2-(5-arylpyridine-2-yl)-6-(het)arylquinoline-based “push-pull” fluorophores
Kopchuk D.S., Chepchugov N.V., Starnovskaya E.S., Khasanov A.F., Krinochkin A.P., Santra S., Zyryanov G.V., Das P., Majee A., Rusinov V.L., Charushin V.N.
Dyes and Pigments, 2019
121.
An efficient synthesis of N-nitrosamines under solvent, metal and acid free conditions using tert-butyl nitrite
Chaudhary P., Gupta S., Muniyappan N., Sabiah S., Kandasamy J.
Green Chemistry, 2016
122.
Nitric Oxide Donors:  Chemical Activities and Biological Applications
Wang P.G., Xian M., Tang X., Wu X., Wen Z., Cai T., Janczuk A.J.
Chemical Reviews, 2002
123.
Nitric oxide donor drugs: current status and future trends
Webb D.J., Megson I.L.
Expert Opinion on Investigational Drugs, 2002
124.
Exogenous donors of nitric oxide (a chemical aspect)
Granik V.G., Grigor"ev N.B.
Russian Chemical Bulletin, 2002
125.
NO problem for nitroglycerin: organic nitrate chemistry and therapy
126.
Cytotoxicity of lysomustine and its isomers, and their potential use for selection of cells
Rozov F.N., Grinenko T.S., Levit G.L., Grishakov A.N., Belyavsky A.V., Krasnov V.P.
Russian Journal of Bioorganic Chemistry, 2011
128.
Reactions of Amides and Sulfonamides with Nitrosonium Salts
Olah G.A., Olah J.A.
Journal of Organic Chemistry, 1965
130.
Conversion of N-Aromatic Amides to O-Aromatic Esters
Glatzhofer D.T., Roy R.R., Cossey K.N.
Organic Letters, 2002
133.
Reduction of nitrosoamides to alcohols using sodium borohydride
136.
Deaminations with nitrogen oxides. New synthesis of alkyl nitrates
Wudl F., Lee T.B.
Journal of the American Chemical Society, 1971
137.
Reaction of N-nitroso- and N-nitro-N-alkylamides with amines
Garcia J., Gonzalez J., Segura R., Urpi F., Vilarrasa J.
Journal of Organic Chemistry, 1984
138.
Syntheses of the benzo[a]naphthacenequinone pigments G-2N and G-2A
Kelly T.R., Xu W., Ma Z., Li Q., Bhushan V.
Journal of the American Chemical Society, 1993
139.
Synthesis of (.+-.)cervinomycins A1 and A2
Kelly T.R., Jagoe C.T., Li Q.
Journal of the American Chemical Society, 1989
140.
Practical synthesis of an enantiomerically pure synthon for the preparation of mevinic acid analogs
Karanewsky D.S., Malley M.F., Gougoutas J.Z.
Journal of Organic Chemistry, 1991
142.
Total synthesis of quinine and quinidine. I
Uskokovic M.R., Gutzwiller J., Henderson T.
Journal of the American Chemical Society, 1970
143.
Advances in the application of N2O4/NO2 in organic reactions
Shiri M., Zolfigol M.A., Kruger H.G., Tanbakouchian Z.
Tetrahedron, 2010
145.
Encapsulated Reagents for Nitrosation
Zyryanov G.V., Rudkevich D.M.
Organic Letters, 2003
146.
Sensing and Fixation of NO2/N2O4 by Calix[4]Arenes
Zyryanov G.V., Kang Y., Rudkevich D.M.
Journal of the American Chemical Society, 2003
147.
Towards Supramolecular Fixation of NOX Gases: Encapsulated Reagents for Nitrosation
Kang Y., Zyryanov G.V., Rudkevich D.M.
Chemistry - A European Journal, 2005
148.
Ionic liquids: a brief history
Welton T.
Biophysical Reviews, 2018
150.
10.1016/j.mencom.2020.09.001_bib0730
Freemantle
An Introduction to Ionic Liquids, 2010
151.
Structure and Nanostructure in Ionic Liquids
Hayes R., Warr G.G., Atkin R.
Chemical Reviews, 2015
152.
Recovery and purification of ionic liquids from solutions: a review
Zhou J., Sui H., Jia Z., Yang Z., He L., Li X.
RSC Advances, 2018
155.
A review of coumarin derivatives in pharmacotherapy of breast cancer.
Musa M., Cooperwood J., Khan M.O.
Current Medicinal Chemistry, 2008
156.
Highly Enantioselective Total Synthesis of (−)-(3′S)-Lomatin and (+)-(3′S,4′R)-trans-Khellactone
Page P.C., Appleby L.F., Day D., Chan Y., Buckley B.R., Allin S.M., McKenzie M.J.
Organic Letters, 2009
158.
Natural and Synthetic 2,2-Dimethylpyranocoumarins with Antibacterial Activity
Melliou E., Magiatis P., Mitaku S., Skaltsounis A., Chinou E., Chinou I.
Journal of Natural Products, 2005
160.
10.1016/j.mencom.2020.09.001_bib0780
Aziridines and Epoxides in Organic Synthesis, 2006
161.
Organocatalysis by an aprotic imidazolium zwitterion: regioselective ring-opening of aziridines and applicable to gram scale synthesis
163.
The Sharpless asymmetric aminohydroxylation
Bodkin J.A., McLeod M.D.
Journal of the Chemical Society Perkin Transactions 1, 2002
165.
A Mild and Efficient Method for the Syntheses and Regioselective Ring-Opening of Aziridines
Ghosal N., Mahato S., Chatterjee R., Santra S., Zyryanov G., Majee A.
SynOpen, 2017
166.
An Updated Library on the Synthesis of Aziridines
Mukherjee A., Ghosal N.C., Zyryanov G.V., Majee A., Santra S.
Current Green Chemistry, 2019
167.
One Century of Aryne Chemistry
Wenk H.H., Winkler M., Sander W.
Angewandte Chemie - International Edition, 2003
168.
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
169.
Use of benzynes for the synthesis of heterocycles
Dubrovskiy A.V., Markina N.A., Larock R.C.
Organic and Biomolecular Chemistry, 2013
170.
Arynes and Cyclohexyne in Natural Product Synthesis
Gampe C.M., Carreira E.M.
Angewandte Chemie - International Edition, 2012
172.
Reactions of Arynes with Nitrosoarenes—An Approach to Substituted Carbazoles
Chakrabarty S., Chatterjee I., Tebben L., Studer A.
Angewandte Chemie - International Edition, 2013
174.
Arynes in the synthesis of polycyclic aromatic hydrocarbons
Wu D., Ge H., Liu S.H., Yin J.
RSC Advances, 2013
175.
Aryne Cycloaddition Reactions in the Synthesis of Large Polycyclic Aromatic Compounds
Pérez D., Peña D., Guitián E.
European Journal of Organic Chemistry, 2013
176.
Benzyne-mediated rearrangement of 3-(2-pyridyl)-1,2,4-triazines into 10-(1H-1,2,3-triazol-1-yl)pyrido[1,2-a]indoles
Nikonov I.L., Kopchuk D.S., Kovalev I.S., Zyryanov G.V., Khasanov A.F., Slepukhin P.A., Rusinov V.L., Chupakhin O.N.
Tetrahedron Letters, 2013
177.
Kopchuk D.S., Nikonov I.L., Zyryanov G.V., Nosova E.V., Kovalev I.S., Slepukhin P.A., Rusinov V.L., Chupakhin O.N.
Mendeleev Communications, 2015
178.
Reaction of 4,5-dimethoxy-1,2-dehydrobenzene with 3-(Pyridin-2-yl)-1,2,4-triazines
Kopchuk D.S., Nikonov I.L., Zyryanov G.V., Kovalev I.S., Taniya O.S., Rusinov V.L., Chupakhin O.N.
Russian Journal of Organic Chemistry, 2015
179.
Studies on the interactions of 5-R-3-(2-pyridyl)-1,2,4-triazines with arynes: inverse demand aza-Diels–Alder reaction versus aryne-mediated domino process
Kopchuk D.S., Nikonov I.L., Khasanov A.F., Giri K., Santra S., Kovalev I.S., Nosova E.V., Gundala S., Venkatapuram P., Zyryanov G.V., Majee A., Chupakhin O.N.
Organic and Biomolecular Chemistry, 2018
180.
Gundala S., Guda M.R., Khasanov A.F., Kopchuk D.S., Krinochkin A.P., Santra S., Zyryanov G.V., Venkatapuram P., Garcia J.R., Charushin V.N.
Mendeleev Communications, 2019
181.
Preparation of 3-Cyano-1-(2-Pyridyl)Isoquinolines by Using Aryne Intermediates
Kopchuk D.S., Nikonov I.L., Zyryanov G.V., Kovalev I.S., Rusinov V.L., Chupakhin O.N.
Chemistry of Heterocyclic Compounds, 2014
182.
2-Azaanthracenes: a chronology of synthetic approaches and bright prospects for practical applications
Taniya O.S., Kopchuk D.S., Khasanov A.F., Kovalev I.S., Santra S., Rahman M., Zyryanov G.V., Majee A., Charushin V.N., Chupakhin O.N.
New Journal of Chemistry, 2019
183.
2-Azaanthracene (microreview)
Taniya O.S., Kopchuk D.S., Khasanov A.F., Kovalev I.S., Zyryanov G.V., Charushin V.N., Chupakhin O.N.
Chemistry of Heterocyclic Compounds, 2019
184.
3-Cyano-2-azaanthracene-based “push-pull” fluorophores: A one-step preparation from 5-cyano-1,2,4-triazines and 2,3-dehydronaphthalene, generated in situ
Kopchuk D.S., Chepchugov N.V., Taniya O.S., Khasanov A.F., Giri K., Kovalev I.S., Santra S., Zyryanov G.V., Majee A., Rusinov V.L., Chupakhin O.N.
Tetrahedron Letters, 2016
185.
Preparation of 1-dichloromethyl- and 1-trichloromethylisoquinolines by a one-step reaction of 1,2,4-triazines with 1,2-dehydrobenzene
Nikonov I.L., Slepukhin P.A., Kopchuk D.S., Kovalev I.S., Zyryanov G.V., Suvorova A.I., Eltsov O.S., Rusinov V.L., Chupakhin O.N.
Chemistry of Heterocyclic Compounds, 2019
186.
One-step synthesis of 1,4-bis(het)arylisoquinolines by the reaction of 1,2,4-triazines with arynes
Kopchuk D.S., Nikonov I.L., Khasanov A.F., Gundala S., Krinochkin A.P., Slepukhin P.А., Zyryanov G.V., Venkatapuram P., Chupakhin O.N., Charushin V.N.
Chemistry of Heterocyclic Compounds, 2019
187.
Kopchuk D.S., Kovalev I.S., Khasanov A.F., Zyryanov G.V., Slepukhin P.A., Rusinov V.L., Chupakhin O.N.
Mendeleev Communications, 2013
188.
Aryne-mediated transformations of 5-perfluorophenyl-substituted 3-(pyridin-2-yl)-1,2,4-triazines in the design of novel 10-(1H-1,2,3-triazol-1-yl)pyrido[1,2-a]indole fluorophores
Moseev T.D., Varaksin M.V., Lavrinchenko I.A., Krinochkin A.P., Kopchuk D.S., Zyryanov G.V., Slepukhin P.A., Chupakhin O.N., Charushin V.N.
Tetrahedron, 2020
190.
СН functionalization of (hetero)arenes with ethyne and ethene moieties
Kopchuk D.S., Taniya O.S., Khasanov A.F., Krinochkin A.P., Kovalev I.S., Pospelova T.A., Zyryanov G.V., Rusinov V.L., Chupakhin O.N.
Chemistry of Heterocyclic Compounds, 2019
191.
10.1016/j.mencom.2020.09.001_bib0935
Charushin
Metal-Free C–H Functionalization of Aromatics: Nucleophilic Displacement of Hydrogen, 2014
192.
Direct introduction of heterocyclic residues into 1,2,4-triazin-5(2H)ones
Rusinov V.L., Zyryanov G.V., Pilicheva T.L., Chupakhin O.N., Neunhoeffer H.
Journal of Heterocyclic Chemistry, 1997
193.
Egorov I.N., Tseitler T.A., Zyryanov G.V., Rusinov V.L., Chupakhin O.N.
Arkivoc, 2011
194.
10.1016/j.mencom.2020.09.001_bib0950
Zyryanov
Russ. J. Org. Chem, 2000
195.
Reaction of 3-phenyl-1,2,4-triazin-5(4H)-one under acylating conditions with natural alcohols containing an asymmetric carbon atom
Egorov I.N., Zyryanov G.V., Slepukhin P.A., Tseitler T.A., Rusinov V.L., Chupakhin O.N.
Chemistry of Heterocyclic Compounds, 2012
196.
Direct diastereoselective addition of l -menthol to activated 1,2,4-triazin-5(4 H )-one
Chupakhin O.N., Zyryanov G.V., Rusinov V.L., Krasnov V.P., Levit G.L., Korolyova M.A., Kodess M.I.
Tetrahedron Letters, 2001
197.
Direct diastereoselective introduction of l-menthol residue into 1,2,4-triazin-5(4H)-one
Zyryanov G.V., Rusinov V.L., Chupakhin O.N., Krasnov V.P., Levit G.L., Kodess M.I., Shtukina T.S.
Russian Chemical Bulletin, 2004
198.
Asymmetric Reactions of a Series of Aromatic Azines with Nucleophiles
N. Egorov I., A. Tseitler T., V. Zyryanov G., L. Rusinov V., N. Chupakhin O.
Heterocycles, 2012
199.
Fatykhov R.F., Savchuk M.I., Starnovskaya E.S., Bobkina M.V., Kopchuk D.S., Nosova E.V., Zyryanov G.V., Khalymbadzha I.A., Chupakhin O.N., Charushin V.N., Kartsev V.G.
Mendeleev Communications, 2019
200.
Direct C H/C Li coupling of 1,2,4-triazines with C6F5Li followed by aza-Diels-Alder reaction as a pot, atom, and step economy (PASE) approach towards novel fluorinated 2,2′-bipyridine fluorophores
Moseev T.D., Varaksin M.V., Gorlov D.A., Nikiforov E.A., Kopchuk D.S., Starnovskaya E.S., Khasanov A.F., Zyryanov G.V., Charushin V.N., Chupakhin O.N.
Journal of Fluorine Chemistry, 2019
201.
Kovalev I.S., Kopchuk D.S., Khasanov A.F., Zyryanov G.V., Rusinov V.L., Chupakhin O.N.
Mendeleev Communications, 2014
202.
New Push-Pull Fluorophores on the Basis of 6-Alkoxy-2,2'-Bipyridines: Rational Synthetic Approach and Photophysical Properties
Savchuk M.I., Khasanov A.F., Kopchuk D.S., Krinochkin A.P., Nikonov I.L., Starnovskaya E.S., Shtaitz Y.K., Kovalev I.S., Zyryanov G.V., Chupakhin O.N.
Chemistry of Heterocyclic Compounds, 2019
203.
6-Arylamino-2,2′-bipyridine “Push-Pull” Fluorophores: Solvent-Free Synthesis and Photophysical Studies
Kopchuk D.S., Krinochkin A.P., Starnovskaya E.S., Shtaitz Y.K., Khasanov A.F., Taniya O.S., Santra S., Zyryanov G.V., Majee A., Rusinov V.L., Chupakhin O.N.
ChemistrySelect, 2018
204.
10.1016/j.mencom.2020.09.001_bib1000
Kopchuk
Res. Chem. Intermed., 2020
205.
New Synthetic Methods to 2-Pyridone Rings
Torres M., Gil S., Parra M.
Current Organic Chemistry, 2005
210.
Efficient one-step synthesis of 3-aryl-2-pyridones from 6-aryl-1,2,4-triazin-5-ones
Savchuk M.I., Shtaitz Y.K., Kopchuk D.S., Zyryanov G.V., Eltsov O.S., Pospelova T.А., Rusinov V.L., Chupakhin O.N.
Chemistry of Heterocyclic Compounds, 2019
211.
10.1016/j.mencom.2020.09.001_bib1035
Varaksin
Makrogeterotsikly/Macroheterocycles, 2013
212.
Photoredox Catalysis for Building C-C Bonds from C(sp2)-H Bonds.
213.
Visible light photoredox catalysis: applications in organic synthesis
Narayanam J.M., Stephenson C.R.
Chemical Society Reviews, 2011
214.
Photoredox Catalysis in Organic Chemistry
Shaw M.H., Twilton J., MacMillan D.W.
Journal of Organic Chemistry, 2016
215.
Visible Light Mediated Photoredox Catalytic Arylation Reactions
Ghosh I., Marzo L., Das A., Shaikh R., König B.
Accounts of Chemical Research, 2016
216.
Visible-Light-Induced Organic Photochemical Reactions through Energy-Transfer Pathways.
Zhou Q., Zou Y., Lu L., Xiao W.
Angewandte Chemie - International Edition, 2018
217.
Organic Photoredox Catalysis
Romero N.A., Nicewicz D.A.
Chemical Reviews, 2016
218.
Dyes as Visible Light Photoredox Organocatalysts
219.
Selective photocatalytic reactions with organic photocatalysts
220.
Visible light-induced C–H sulfenylation using sulfinic acids
Sun P., Yang D., Wei W., Jiang M., Wang Z., Zhang L., Zhang H., Zhang Z., Wang Y., Wang H.
Green Chemistry, 2017
221.
Visible-Light-Induced Regioselective C(sp3)-H Acyloxylation of Aryl-2H-azirines with (Diacetoxy)iodobenzene
De A., Santra S., Hajra A., Zyryanov G.V., Majee A.
Journal of Organic Chemistry, 2019
222.
Meglumine as a green, efficient and reusable catalyst for synthesis and molecular docking studies of bis(indolyl)methanes as antioxidant agents
Nemallapudi B.R., Zyryanov G.V., Avula B., Guda M.R., Cirandur S.R., Venkataramaiah C., Rajendra W., Gundala S.
Bioorganic Chemistry, 2019
223.
Pyranopyrazoles as efficient antimicrobial agents: Green, one pot and multicomponent approach
Reddy G.M., Garcia J.R., Zyryanov G.V., Sravya G., Reddy N.B.
Bioorganic Chemistry, 2019
224.
Environmentally benign one-pot multicomponent synthesis of 1,4-dihydropyridine derivatives applying montmorillonite K10 as reusable catalyst
Reddy V.H., Kumari A.K., Reddy G.M., Reddy Y.V., Garcia J.R., Zyryanov G.V., Reddy N.B., Rammohan A.
Chemistry of Heterocyclic Compounds, 2019
225.
Ball milling: an efficient and green approach for asymmetric organic syntheses
Egorov I.N., Santra S., Kopchuk D.S., Kovalev I.S., Zyryanov G.V., Majee A., Ranu B.C., Rusinov V.L., Chupakhin O.N.
Green Chemistry, 2020
226.
Laser-driven heterogeneous catalysis: efficient amide formation catalysed by Au/SiO2 systems
Pineda A., Gomez L., Balu A.M., Sebastian V., Ojeda M., Arruebo M., Romero A.A., Santamaria J., Luque R.
Green Chemistry, 2013
227.
10.1016/j.mencom.2020.09.001_bib1115
McNab
Aldrichim. Acta, 2004
231.
Chemical amplification with encapsulated reagents
Chen J., Körner S., Craig S.L., Lin S., Rudkevich D.M., Rebek J.
Proceedings of the National Academy of Sciences of the United States of America, 2002
232.
Safe storage of radical initiators within a polyaromatic nanocapsule
Yamashina M., Sei Y., Akita M., Yoshizawa M.
Nature Communications, 2014
236.
10.1016/j.mencom.2020.09.001_bib1160
Chupakhin
2020