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Ring-opening of pyridines and imidazoles with electron-deficient acetylenes: En route to metal-free organic synthesis

Boris Aleksandrovich Trofimov 1
Boris Aleksandrovich Trofimov
,  , 
Ludmila Viktorovna Andriyankova 1
Ludmila Viktorovna Andriyankova
, 
Lina Pavlovna Nikitina 1
Lina Pavlovna Nikitina
, 
Anastasiya Grigor'evna Mal'kina 1
Anastasiya Grigor'evna Mal'kina
10.1016/j.mencom.2017.03.001
Published 2017-02-27
Focus article , Volume 27, Issue 2, 109-115
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Trofimov B. A. et al. Ring-opening of pyridines and imidazoles with electron-deficient acetylenes: En route to metal-free organic synthesis // Mendeleev Communications. 2017. Vol. 27. No. 2. pp. 109-115.
GOST all authors (up to 50) Copy
Trofimov B. A., Belyaeva K. V., Andriyankova L. V., Nikitina L. P., Mal'kina A. G. Ring-opening of pyridines and imidazoles with electron-deficient acetylenes: En route to metal-free organic synthesis // Mendeleev Communications. 2017. Vol. 27. No. 2. pp. 109-115.
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TY - JOUR
DO - 10.1016/j.mencom.2017.03.001
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2017.03.001
TI - Ring-opening of pyridines and imidazoles with electron-deficient acetylenes: En route to metal-free organic synthesis
T2 - Mendeleev Communications
AU - Trofimov, Boris Aleksandrovich
AU - Belyaeva, Kseniya Vasil'evna
AU - Andriyankova, Ludmila Viktorovna
AU - Nikitina, Lina Pavlovna
AU - Mal'kina, Anastasiya Grigor'evna
PY - 2017
DA - 2017/02/27
PB - Mendeleev Communications
SP - 109-115
IS - 2
VL - 27
ER -
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@article{2017_Trofimov,
author = {Boris Aleksandrovich Trofimov and Kseniya Vasil'evna Belyaeva and Ludmila Viktorovna Andriyankova and Lina Pavlovna Nikitina and Anastasiya Grigor'evna Mal'kina},
title = {Ring-opening of pyridines and imidazoles with electron-deficient acetylenes: En route to metal-free organic synthesis},
journal = {Mendeleev Communications},
year = {2017},
volume = {27},
publisher = {Mendeleev Communications},
month = {Feb},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2017.03.001},
number = {2},
pages = {109--115},
doi = {10.1016/j.mencom.2017.03.001}
}
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Trofimov, Boris Aleksandrovich, et al. “Ring-opening of pyridines and imidazoles with electron-deficient acetylenes: En route to metal-free organic synthesis.” Mendeleev Communications, vol. 27, no. 2, Feb. 2017, pp. 109-115. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2017.03.001.
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Abstract

The article is focused on the recently developed methodology for the efficient synthesis of diverse highly unsaturated previously unknown highly functionalized enamines, which comprises the mild transition-metal free hydrative ringopening of pyridines and imidazoles proceeding via zwitterionic adducts of these heterocycles with electron-deficient acetylenes. The synthesized compounds are of high synthetic and pharmaceutical value being promising intermediates for drug design.

References

1.
Ananikov V.P., Galkin K.I., Egorov M.P., Sakharov A.M., Zlotin S.G., Redina E.A., Isaeva V.I., Kustov L.M., Gening M.L., Nifantiev N.E.
Mendeleev Communications, 2016
2.
Acetylene: new prospects of classical reactions
Trofimov B.A., Gusarova N.K.
Russian Chemical Reviews, 2007
4.
Catalytic reactions of acetylene: a feedstock for the chemical industry revisited.
Trotuş I., Zimmermann T., Schüth F.
Chemical Reviews, 2013
5.
Reactions of acetylenes in superbasic media. Recent advances
Trofimov B.A., Schmidt E.Y.
Russian Chemical Reviews, 2014
7.
10.1016/j.mencom.2017.03.001_bib0035
Gusarova
Khimiya at setilena. Novye glavy (The Chemistry of Acetylene. New Chapters), 2013
10.
10.1016/j.mencom.2017.03.001_bib0050
Trofimov
Chemistry of Pyrroles, 2015
11.
Organic Superbases in Annulation with Propargylic Alcohols: Straightforward Synthesis of the Functionalized Oxazolopyrrolohexahydropyrimidine and Oxazolohexahydropyrimidoazepine Scaffolds
Trofimov B.A., Shemyakina O.A., Mal'kina A.G., Stepanov A.V., Volostnykh O.G., Ushakov I.A., Vashchenko A.V.
European Journal of Organic Chemistry, 2016
12.
10.1016/j.mencom.2017.03.001_bib0060
Trofimov
2009
13.
C-Ethynylpyrroles: synthesis and reactivity
Sobenina L.N., Tomilin D.N., Trofimov B.A.
Russian Chemical Reviews, 2014
14.
Direct synthesis of butadiynyl-substituted pyrroles under solvent- and transition metal-free conditions
Tomilin D.N., Pigulski B., Gulia N., Arendt A., Sobenina L.N., Mikhaleva A.I., Szafert S., Trofimov B.A.
RSC Advances, 2015
15.
Transition-Metal Free Mechanochemical Approach to Polyyne Substituted Pyrroles
Pigulski B., Arendt A., Tomilin D.N., Sobenina L.N., Trofimov B.A., Szafert S.
Journal of Organic Chemistry, 2016
16.
A Domino Reaction of α,β-Acetylenic γ-Hydroxy Nitriles with Arenecarboxylic Acids: An Unexpected Facile Shortcut to 4-Cyano-3(2H)-furanones
Trofimov B.A., Shemyakina O.A., Mal’kina A.G., Ushakov I.A., Kazheva O.N., Alexandrov G.G., Dyachenko O.A.
Organic Letters, 2010
17.
Chemo-, regio- and stereospecific addition of adenine and 8-azaadenine to α,β-acetylenic γ-hydroxy nitriles: a short-cut to novel acyclic adenosine analogues
Trofimov B.A., Mal'kina A.G., Nosyreva V.V., Shemyakina O.A., Borisova A.P., Larina L.I., Kazheva O.N., Alexandrov G.G., Dyachenko O.A.
Tetrahedron, 2010
18.
Mal’kina A.G., Nosyreva V.V., Shemyakina O.A., Albanov A.I., Trofimov B.A.
Mendeleev Communications, 2017
19.
One-Pot Assembly of 7-Methylene-6,8-dioxabicyclo[3.2.1]octanes, Congeners of Frontalin, from Ketones and Acetylene
Trofimov B.A., Schmidt E.Y., Ushakov I.A., Mikhaleva A.I., Zorina N.V., Protsuk N.I., Senotrusova E.Y., Skital'tseva E.V., Kazheva O.N., Alexandrov G.G., Dyachenko O.A.
European Journal of Organic Chemistry, 2009
21.
Stereoselective Tandem Ring Opening of Imidazoles with Electron-Deficient Acetylenes and Water: Synthesis of Functionalized (Z,Z)-1,4-Diaza-2,5-dienes
Trofimov B.A., Andriyankova L.V., Nikitina L.P., Belyaeva K.V., Mal’kina A.G., Sobenina L.N., Afonin A.V., Ushakov I.A.
Organic Letters, 2013
22.
Superbase-Catalyzed [4+2] Cycloaddition of Acetylenes to 3,6-Di(pyrrol-2-yl)-1,2,4,5-tetrazine: A Facile Synthesis of 3,6-Di(pyrrol-2-yl)pyridazines
Trofimov B.A., Glotova T.E., Shabalin D.A., Dvorko M.Y., Ushakov I.A., Schmidt E.Y., Kuzmin A.V., Mikhaleva A.I.
Advanced Synthesis and Catalysis, 2013
23.
Superbase-Promoted Selective Cascade Cyclization Reaction of 1,5-Diketones with Acetylenes to Methylene-6,8-dioxabicyclo[3.2.1]octanes
Schmidt E.Y., Bidusenko I.A., Protsuk N.I., Ushakov I.A., Trofimov B.A.
European Journal of Organic Chemistry, 2013
24.
Synthesis of Acyl Terphenyls and Higher Polyaromatics via Base-Promoted C–H Functionalization of Acetylarenes with Arylacetylenes
Schmidt E.Y., Ivanova E.V., Tatarinova I.V., Ushakov I.A., Semenova N.V., Vashchenko A.V., Trofimov B.A.
Organic Letters, 2016
25.
Base-Catalyzed Domino Cyclization of Acetylenes with Ketones to Functionalized Cyclopentenes
Schmidt E.Y., Trofimov B.A., Bidusenko I.A., Cherimichkina N.A., Ushakov I.A., Protzuk N.I., Gatilov Y.V.
Organic Letters, 2014
26.
Furans Conjugated with Bulky Aromatic Systems: One‐Pot Synthesis from Ketones and Acetylene
Schmidt E.Y., Bidusenko I.A., Cherimichkina N.A., Ushakov I.A., Borodina T.N., Smirnov V.I., Trofimov B.A.
Chemistry - A European Journal, 2015
28.
Vereshchagin A.N., Elinson M.N., Anisina Y.E., Ryzhkov F.V., Goloveshkin A.S., Bushmarinov I.S., Zlotin S.G., Egorov M.P.
Mendeleev Communications, 2015
29.
A facile annelation of pyridines with nitriles of α,β-acetylenic γ-hydroxyacids
Trofimov B.A., Andriyankova L.V., Zhivet'ev S.A., Mal'kina A.G., Voronov V.K.
Tetrahedron Letters, 2002
30.
Reaction of 3-(1-Hydroxycyclohexyl)-2-propynenitrile with Tris[2-(4-pyridyl)ethyl]phosphine Oxide
Trofimov B.A., Andriyankova L.V., Shaikhudinova S.I., Kazantseva T.I., Mal’kina A.G., Afonin A.V.
Synthesis, 2002
31.
Andriyankova L.V., Mal’kina A.G., Afonin A.V., Trofimov B.A.
Mendeleev Communications, 2003
32.
Regio- and stereoselective annelation of phenanthridines with α,β-acetylenic γ-hydroxyacid nitriles
Andriyankova L.V., Mal'kina A.G., Nikitina L.P., Belyaeva K.V., Ushakov I.A., Afonin A.V., Nikitin M.V., Trofimov B.A.
Tetrahedron, 2005
33.
Trofimov B.A., Andriyankova L.V., Tlegenov R.T., Mal’kina A.G., Afonin A.V., Il’icheva L.N., Nikitina L.P.
Mendeleev Communications, 2005
35.
10.1016/j.mencom.2017.03.001_bib0175
Belyaeva
Mendeleev Commun., 2014
36.
Dimethyl Acetylenedicarboxylate: A Versatile Tool in Organic Synthesis
Stephanidou-Stephanatou J., Neochoritis C., Zarganes-Tzitzikas T.
Synthesis, 2014
37.
One-pot reductive N-vinylation and C(4)-phosphorylation of pyridines with alkyl propiolates and secondary phosphine chalcogenides
Gusarova N.K., Volkov P.A., Ivanova N.I., Arbuzova S.N., Khrapova K.O., Albanov A.I., Smirnov V.I., Borodina T.N., Trofimov B.A.
Tetrahedron Letters, 2015
38.
Efficient synthesis of novel Pyrroloquinoline derivatives
Kalantari S., Piltan M., Zarei S.A.
Journal of the Iranian Chemical Society, 2015
40.
Annelation of Benzimidazoles with α,β-Acetylenic γ-Hydroxyacid Nitriles and Hydrolytic Rearrangement of the Cycloadducts on Alumina
Trofimov B.A., Andriyankova L.V., Mal'kina A.G., Belyaeva K.V., Nikitina L.P., Dyachenko O.A., Kazheva O.N., Chekhlov A.N., Shilov G.V., Afonin A.V., Ushakov I.A., Baikalova L.V.
European Journal of Organic Chemistry, 2007
42.
10.1016/j.mencom.2017.03.001_bib0210
Andriyankova
Synthesis, 2010
44.
New methodology for functionalization of the imidazole ring by alkynes
Trofimov B.A., Andriyankova L.V., Belyaeva K.V.
Chemistry of Heterocyclic Compounds, 2012
45.
Trofimov B.A., Andriyankova L., Nikitina L., Belyaeva K., Malkina A., Dyachenko O., Kazheva O., Chekhlov A., Afonin A.
Arkivoc, 2012
46.
10.1016/j.mencom.2017.03.001_bib0230
Trofimov
Vestnik SPbGU, Ser. 4, 2014
47.
Stereoselective Synthesis of N-[(Z)-2-Cyano-1-Phenylethenyl]Benzimidazole-2-Carbothioamides by a Three-Component Reaction of 1-Substituted Benzimidazoles, Phenylcyanoacetylene, and Isothiocyanates
Andriyankova L.V., Nikitina L.P., Belyaeva K.V., Mal’kina A.G., Afonin A.V., Vashchenko A.V., Smirnov V.I., Trofimov B.A.
Chemistry of Heterocyclic Compounds, 2014
48.
(Imidazol-2-yl)methyl-1,3-propanediones: Regioselective C-H Functionalization of the Imidazole Ring by Acylacetylene/Aldehyde Pairs
Trofimov B.A., Andriyankova L.V., Nikitina L.P., Belyaeva K.V., Mal'kina A.G., Bagryanskaya I.Y., Afonin A.V., Ushakov I.A.
European Journal of Organic Chemistry, 2016
49.
10.1016/j.mencom.2017.03.001_bib0245
Zincke
Justus Liebigs Ann. Chem., 1903
52.
Photochromic behavior of several new synthesized dyes via Zincke salts
Mahmoodi N.O., Mamaghani M., Ghanadzadeh A., Arvand M., Fesanghari M.
Journal of Physical Organic Chemistry, 2009
53.
10.1016/j.mencom.2017.03.001_bib0265
Nguyen
Synthesis, 2010
54.
10.1016/j.mencom.2017.03.001_bib0270
Delpech
2014
56.
VT-NMR and cytotoxic evaluation of some new ortho-(alkylchalcogen)acetanilides
Ramos S.S., Almeida S.S., Leite P.M., Boto R.E., Silvestre S., Almeida P.
Tetrahedron, 2014
57.
A facile synthesis of 2-(trifluoromethyl)histamine and 2-(trifluoromethyl)-L-histidine
Kimoto H., Kirk K.L., Cohen L.A.
Journal of Organic Chemistry, 1978
60.
Reactions of Aminopentadienal Derivatives with 5,6-Dihydropyridinium Salts as an Approach to Manzamine Alkaloids Based upon Biogenetic Considerations
Jakubowicz K., Abdeljelil K.B., Herdemann M., Martin M., Gateau-Olesker A., Mourabit A.A., Marazano C., Das B.C.
Journal of Organic Chemistry, 1999
61.
Further Insight from Model Experiments into a Possible Scenario Concerning the Origin of Manzamine Alkaloids
Wypych J., Nguyen T., Nuhant P., Bénéchie M., Marazano C.
Angewandte Chemie - International Edition, 2008
62.
Synthesis of the Indolic Pentacyclic Core of Manadomanzamine A Following Biogenetically Based Strategies
Yan L., Nuhant P., Sinigaglia I., Fromentin Y., Marazano C., Delpech B., Poupon E.
European Journal of Organic Chemistry, 2012
64.
A Zincke aldehyde approach to gelsemine
Lam J.K., Joseph S.B., Vanderwal C.D.
Tetrahedron Letters, 2015
68.
Synthesis of L-(+)-Ergothioneine
Xu J., Yadan J.C.
Journal of Organic Chemistry, 1995
70.
Opening of pyridine ring with benzoyl(phenyl)acetylene in the presence of water with formation of 5-aminopenta-2,4-dienal
Trofimov B.A., Andriyankova L.V., Nikitina L.P., Belyaeva K.V., Mal’kina A.G., Afonin A.V.
Russian Journal of Organic Chemistry, 2015
71.
Ring‐Opening of Pyridines with Acyl­acetylenes and Water: Straightforward Access to 5‐[(Z)‐Acylethenyl]amino‐2,4‐pentadienals
Trofimov B.A., Andriyankova L.V., Belyaeva K.V., Nikitina L.P., Afonin A.V., Mal'kina A.G.
European Journal of Organic Chemistry, 2015
72.
10.1016/j.mencom.2017.03.001_bib0365
Andriyankova
Zh. Org. Khim., 2016
73.
10.1016/j.mencom.2017.03.001_bib0370
Miller
1970
74.
10.1016/j.mencom.2017.03.001_bib0375
Dickstein
1978
75.
10.1016/j.mencom.2017.03.001_bib0380
Smith
1979
77.
Synthesis of Nitrogen Heterocycles by the Ring Opening of Pyridinium Salts
Kearney A.M., Vanderwal C.D.
Angewandte Chemie - International Edition, 2006
79.
10.1016/j.mencom.2017.03.001_bib0400
Kirsch
Modern Fluoroorganic Chemistry: Synthesis, Reactivity, Applications, 2013
80.
10.1016/j.mencom.2017.03.001_bib0405
Gribble
Progress in Heterocyclic Chemistry, 2015
81.
10.1016/j.mencom.2017.03.001_bib0410
Aly
2014
82.
Ytterbocenes as One- and Two-Electron Reductants in their Reactions with Diazadienes: YbIII Mixed-Ligand Bent-Sandwich Complexes Containing a Dianion of Diazabutadiene
Trifonov A., Borovkov I., Fedorova E., Fukin G., Larionova J., Druzhkov N., Cherkasov V.
Chemistry - A European Journal, 2007
85.
10.1016/j.mencom.2017.03.001_bib0435
Cruz-Acosta
Synlett, 2010
86.
Hydrolysis of Imidazole-2-ylidenes
Hollóczki O., Terleczky P., Szieberth D., Mourgas G., Gudat D., Nyulászi L.
Journal of the American Chemical Society, 2010
87.
Stable N-Heterocyclic Carbenes: N-Alkyl-N′-phosphanylbenzimidazol-2-ylidenes
Marchenko A.P., Koidan H.N., Hurieva A.N., Pervak I.I., Shishkina S.V., Shishkin O.V., Kostyuk A.N.
European Journal of Organic Chemistry, 2012
88.
C2-Functionalization of 1-Substituted Imidazoles with Aldehydes and Electron-Deficient Acetylenes: A Novel Three-Component Reaction
Trofimov B.A., Andriyankova L.V., Belyaeva K.V., Mal'kina A.G., Nikitina L.P., Afonin A.V., Ushakov I.A.
European Journal of Organic Chemistry, 2010
89.
Anticonvulsant evaluation and mechanism of action of benzylamino enaminones
Edafiogho I.O., Ananthalakshmi K.V., Kombian S.B.
Bioorganic and Medicinal Chemistry, 2006
91.
Synthesis and antitumor activity of novel pyrazolylenaminone and bis(pyrazolyl)ketonesviahydrazonoyl halides
Shawali A.S., Sherif S.M., El-Merzabani M.M., Darwish M.A.
Journal of Heterocyclic Chemistry, 2009
92.
Reaction of 1-substituted benzimidazoles with acylacetylenes and water: ring-opening versus ring-expansion and isotopic effect of deuterium
Belyaeva K.V., Andriyankova L.V., Nikitina L.P., Bagryanskaya I.Y., Afonin A.V., Ushakov I.A., Mal'kina A.G., Trofimov B.A.
Tetrahedron, 2015
93.
Belyaeva K.V., Andriyankova L.V., Nikitina L.P., Afonin A.V., Ushakov I.A., Mal’kina A.G., Trofimov B.A.
Mendeleev Communications, 2015
95.
Trofimov B.A., Nikitina L.P., Belyaeva K.V., Andriyankova L.V., Mal’kina A.G., Bagryanskaya I.Y., Afonin A.V., Ushakov I.A.
Mendeleev Communications, 2016
96.
Exceptionally Easy Ring Cleavage of Benzimidazoles by α,β-Acetylenic γ-Hydroxy Nitriles and Water
Trofimov B., Andriyankova L., Nikitina L., Belyaeva K., Mal’kina A., Afonin A.
Synthesis, 2010
97.
Discovery of Benzylidenebenzofuran-3(2H)-one (Aurones) as Inhibitors of Tyrosinase Derived from Human Melanocytes
Okombi S., Rival D., Bonnet S., Mariotte A., Perrier E., Boumendjel A.
Journal of Medicinal Chemistry, 2005
98.
Synthesis of Dihydrofurans Substituted in the 2‐Position
Kilroy T.G., O'Sullivan T.P., Guiry P.J.
European Journal of Organic Chemistry, 2005
99.
The Selectivity of Austocystin D Arises from Cell-Line-Specific Drug Activation by Cytochrome P450 Enzymes
Marks K.M., Park E.S., Arefolov A., Russo K., Ishihara K., Ring J.E., Clardy J., Clarke A.S., Pelish H.E.
Journal of Natural Products, 2011