Abstract:
1,3-Diphenylprop-2-yn-1-one is inserted into 3-substituted imidazo[4,5-b]pyridines upon refluxing in MeCN in the presence of equimolar amount of water to afford pyrido[2,3-b][1,4]diazocin-9-ones in up to 61% yield.
Citation:
B. A. Trofimov, L. P. Nikitina, K. V. Belyaeva, L. V. Andriyankova, A. G. Mal'kina, I. Yu. Bagryanskaya, A. V. Afonin, I. A. Ushakov, “Insertion of 1,3-diphenylprop-2-yn-1-one into imidazo[4,5-b]pyridines in the presence of water: one-pot synthesis of pyrido[2,3-b][1,4]diazocin-9-ones”, Mendeleev Commun., 26:1 (2016), 16–18
Linking options:
https://www.mathnet.ru/eng/mendc2094
https://www.mathnet.ru/eng/mendc/v26/i1/p16
This publication is cited in the following 9 articles:
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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
M. G. Moloney, Organic Reaction Mechanisms Series, Organic Reaction Mechanisms · 2016, 2020, 201
J. M. Coxon, Organic Reaction Mechanisms Series, Organic Reaction Mechanisms · 2016, 2020, 697
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
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
N. K. Gusarova, P. A. Volkov, N. I. Ivanova, K. O. Khrapova, A. A. Telezhkin, A. I. Albanov, B. A. Trofimov, “Structural effect in the reductive vinylation/phosphorylation of pyridines with alkyl propiolates and secondary phosphine chalcogenides: protonation vs. zwitterion generation”, Mendeleev Commun., 27:6 (2017), 553–555
Boris A. Trofimov, Lina P. Nikitina, Kseniya V. Belyaeva, Ludmila V. Andriyankova, Anastasiya G. Mal'kina, Irina Yu. Bagryanskaya, Andrei V. Afonin, Igor A. Ushakov, “ChemInform Abstract: Insertion of 1,3‐Diphenylprop‐2‐yn‐1‐one into Imidazo[4,5‐b]pyridines in the Presence of Water: One‐Pot Synthesis of Pyrido[2,3‐b][1,4]diazocin‐9‐ones.”, ChemInform, 47:24 (2016)