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.
Document Type:
Article
Language: English
Citation:
B. A. Trofimov, K. V. Belyaeva, L. V. Andriyankova, L. P. Nikitina, A. G. Mal'kina, “Ring-opening of pyridines and imidazoles with electron-deficient acetylenes: En route to metal-free organic synthesis”, Mendeleev Commun., 27:2 (2017), 109–115
Linking options:
https://www.mathnet.ru/eng/mendc1913
https://www.mathnet.ru/eng/mendc/v27/i2/p109
This publication is cited in the following 17 articles:
Jing Wang, Lu Ren, Chang Liu, Yanqi Liu, Yujie Shang, Yulu Zhang, Dawei Zhang, “Colorimetric Fluorescence of a 2,4,5‐Triaryl Imidazole‐Based Sensor for the Selective Detection of Iron”, ChemistrySelect, 9:24 (2024)
V. N. Charushin, E. V. Verbitskiy, O. N. Chupakhin, D. V. Vorobyeva, P. S. Gribanov, S. N. Osipov, A. V. Ivanov, S. V. Martynovskaya, E. F. Sagitova, V. D. Dyachenko, I. V. Dyachenko, S. G. Krivokolylsko, V. V. Dotsenko, A. V. Aksenov, D. A. Aksenov, N. A. Aksenov, A. A. Larin, L. L. Fershtat, V. M. Muzalevskiy, V. G. Nenajdenko, A. V. Gulevskaya, A. F. Pozharskii, E. A. Filatova, K. V. Belyaeva, B. A. Trofimov, I. A. Balova, N. A. Danilkina, A. I. Govdi, A. S. Tikhomirov, A. E. Shchekotikhin, M. S. Novikov, N. V. Rostovskii, A. F. Khlebnikov, Yu. N. Klimochkin, M. V. Leonova, I. M. Tkachenko, V. A.-o. Mamedov, V. L. Mamedova, N. A. Zhukova, V. E. Semenov, O. G. Sinyashin, O. V. Borshchev, Yu. N. Luponosov, S. A. Ponomarenko, A. S. Fisyuk, A. S. Kostyuchenko, V. G. Ilkin, T. V. Beryozkina, V. A. Bakulev, A. S. Gazizov, A. A. Zagidullin, A. A. Karasik, M. E. Kukushkin, E. K. Beloglazkina, N. E. Golantsov, A. A. Festa, L. G. Voskresenskii, V. S. Moshkin, E. M. Buev, V. Ya. Sosnovskikh, I, “The chemistry of heterocycles in the 21st century”, Russian Chem. Reviews, 93:7 (2024), RCR5125
Pavel A. Volkov, Kseniya O. Khrapova, Anton A. Telezhkin, Alexander I. Albanov, Boris A. Trofimov, “Synthesis of polyfluoroalkylphosphorylated dihydroquinolines and dihydroisoquinolines decorated with N-acylethenyl substituents by the reaction of bis(polyfluoroalkyl)phosphonates with electron-deficient acetylenes and quinolines”, Journal of Fluorine Chemistry, 270 (2023), 110172
Ludmila A. Oparina, Anastasiya G. Mal'kina, Nikita A. Kolyvanov, Igor A. Ushakov, Ivan V. Saliy, Konstantin A. Apartsin, Boris A. Trofimov, “δ-Keto Aminoacrylonitriles and δ-Keto Aminoenones from 1-Pyrrolines, Cyanoacetylenes, and Acetylenic Ketones”, Synthesis, 54:11 (2022), 2635
G. Varvounis, V. Gkalpinos, P. Theodorakopoulou, E. Tsemperlidou, Comprehensive Heterocyclic Chemistry IV, 2022, 113
Tarek A. Mohamed, Ibrahim A. Shaaban, Usama A. Soliman, Wajdi M. Zoghaib, “2‐Hydroxy‐5‐nitropyridine and 5‐nitro‐2‐pyridone: Tautomerism, infrared, Raman, and NMR spectral interpretations, normal coordinate analysis, and DFT calculations”, J Chinese Chemical Soc, 68:10 (2021), 1863
Boris A. Trofimov, Kseniya V. Belyaeva, “Zwitterionic adducts of N-heterocycles to electrophilic acetylenes as a master key to diversity and complexity of fundamental nitrogen heterocycles”, Tetrahedron Letters, 61:24 (2020), 151991
Vasiliy M. Muzalevskiy, Zoia A. Sizova, Kseniya V. Belyaeva, Boris A. Trofimov, Valentine G. Nenajdenko, “One-Pot Metal-Free Synthesis of 3-CF3-1,3-Oxazinopyridines by Reaction of Pyridines with CF3CO-Acetylenes”, Molecules, 24:19 (2019), 3594
Leonid I. Belen'kii, Yulia. B. Evdokimenkova, Advances in Heterocyclic Chemistry, 129, 2019, 337
L. V. Politanskaya, G. A. Selivanova, E. V. Panteleeva, E. V. Tretyakov, V. E. Platonov, P. V. Nikul'shin, A. S. Vinogradov, Ya. V. Zonov, V. M. Karpov, T. V. Mezhenkova, A. V. Vasilyev, A. B. Koldobskii, O. S. Shilova, S. M. Morozova, Ya. V. Burgart, E. V. Shchegolkov, V. I. Saloutin, V. B. Sokolov, A. Yu. Aksinenko, V. G. Nenajdenko, M. Yu. Moskalik, V. V. Astakhova, B. A. Shainyan, A. A. Tabolin, S. L. Ioffe, V. M. Muzalevskiy, E. S. Balenkova, A. V. Shastin, A. A. Tyutyunov, V. E. Boiko, S. M. Igumnov, A. D. Dilman, N. Yu. Adonin, V. V. Bardin, S. M. Masoud, D. V. Vorobyeva, S. N. Osipov, E. V. Nosova, G. N. Lipunova, V. N. Charushin, D. O. Prima, A. G. Makarov, A. V. Zibarev, B. A. Trofimov, L. N. Sobenina, K. V. Belyaeva, V. Ya. Sosnovskikh, D. L. Obydennov, S. A. Usachev, “Organofluorine chemistry: promising growth areas and challenges”, Russian Chem. Reviews, 88:5 (2019), 425–569
K. V. Belyaeva, L. P. Nikitina, A. V. Afonin, B. A. Trofimov, “Simultaneous Double C2/C3 Functionalization of Quinoline with p-Nitrobenzoyl(phenyl)acetylene. One-Pot Synthesis of 3-(4-Nitrobenzoyl)-2-phenylquinoline”, Russ J Org Chem, 54:12 (2018), 1845
B. A. Trofimov, K. V. Belyaeva, L. P. Nikitina, A. G. Mal'kina, A. V. Afonin, I. A. Ushakov, A. V. Vashchenko, “Transition metal-free one-pot double C–H functionalization of quinolines with disubstituted electron-deficient acetylenes”, Chem. Commun., 54:46 (2018), 5863
K. V. Belyaeva, L. P. Nikitina, A. V. Afonin, A. V. Vashchenko, V. M. Muzalevskiy, V. G. Nenajdenko, B. A. Trofimov, “Catalyst-free 1 : 2 annulation of quinolines with trifluoroacetylacetylenes: an access to functionalized oxazinoquinolines”, Org. Biomol. Chem., 16:43 (2018), 8038
E. Yu. Schmidt, I. V. Tatarinova, N. I. Protsuk, I. A. Ushakov, B. A. Trofimov, “Dioximes of 1,6-heptanediones from acetylene and ketones: only three atom-economic steps”, Mendeleev Commun., 28:2 (2018), 143–144
E. Yu. Schmidt, I. A. Bidusenko, N. A. Cherimichkina, B. A. Trofimov, “Acetylene as driving and organizing molecule in the assembling reactions with chalcones in the NaOBut/DMSO superbase system”, Mendeleev Commun., 28:1 (2018), 47–48
B. A. Trofimov, K. V. Belyaeva, L. P. Nikitina, A. V. Afonin, A. V. Vashchenko, “2-(5-Arylterphenyl-4-yl)quinolines from 2-methylquinoline and 1-(het)aryl-3-phenylprop-2-yn-1-ones in just a one step: A miracle of molecular interplay”, Mendeleev Commun., 28:3 (2018), 267–269
K. V. Belyaeva, L. P. Nikitina, A. V. Afonin, A. V. Vashchenko, B. A. Trofimov, “Reaction of 2-methylquinoline with 3-phenylprop-2-ynenitrile in the KOH—H2O system”, Russ Chem Bull, 66:12 (2017), 2258