Abstract:
5-Alkynyl-6-aryl-2,2′-bipyridines were conveniently prepared in two steps comprising oxidative SN H ethynylation of 5-aryl-3-(2-pyridyl)-1,2,4-triazines at position 6. At the second step, the 1,2,4-triazine moiety was transformed into the pyridine one employing aza-Diels–Alder reaction with 2,5-norbornadiene.
Keywords:
nucleophilic substitution of hydrogen, 1,2,4-triazines, acetylenes, 2,2′-bipyridines, aza-Diels–Alder reaction.
Citation:
M. I. Savchuk, A. P. Krinochkin, A. Rammohan, A. F. Khasanov, D. S. Kopchuk, I. N. Egorov, S. Santra, G. V. Zyryanov, V. L. Rusinov, O. N. Chupakhin, “An expedient synthesis of 5-alkynyl-6-aryl-2,2′-bipyridines”, Mendeleev Commun., 30:5 (2020), 610–611
Linking options:
https://www.mathnet.ru/eng/mendc1268
https://www.mathnet.ru/eng/mendc/v30/i5/p610
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Aluru Rammohan, Albert F. Khasanov, Dmitry S. Kopchuk, Duvvuru Gunasekar, Grigory V. Zyryanov, Oleg N. Chupakhin, “Assessment on facile Diels–Alder approach of α-pyrone and terpenoquinone for the expedient synthesis of various natural scaffolds”, Nat. Prod. Bioprospect., 12:1 (2022)
A. Rammohan, A. P. Krinochkin, D. S. Kopchuk, Ya. K. Shtaitz, I. S. Kovalev, M. I. Savchuk, G. V. Zyryanov, V. L. Rusinov, O. N. Chupakhin, “Conditions for the Synthesis of 4,5-Diaryl-3-hydroxy-2,2'-bipyridine-6-carbonitriles by the Reaction of 1,2,4-Triazine-5-carbonitriles with 2-Aminooxazoles”, Russ J Org Chem, 58:2 (2022), 175
Alexey P. Krinochkin, Yaroslav K. Shtaitz, Aluru Rammohan, Ilya I. Butorin, Maria I. Savchuk, Igor A. Khalymbadzha, Dmitry S. Kopchuk, Pavel A. Slepukhin, Vsevolod V. Melekhin, Anna V. Shcheglova, Grigory V. Zyryanov, Oleg N. Chupakhin, “1H‐Pyrazole‐Appended Pyridines and Their 1,2,4‐Triazine Precursors: A Rational Synthesis and in silico and in vitro Evaluation of Anti‐Cancer Activity”, Eur J Org Chem, 2022:22 (2022)
A. P. Krinochkin, M. R. Guda, A. Rammohan, D. S. Kopchuk, I. L. Nikonov, E. D. Ladin, S. Santra, I. N. Egorov, G. V. Zyryanov, O. N. Chupakhin, “Synthesis of 2-amino-3,6-di(het)arylpyridines from 5-cyano-3,6-di(het)aryl-1,2,4-triazines and arylhydrazines via the
$\mathrm{S_N^{ipso}}$/aza-Diels–Alder reaction sequence”, Mendeleev Commun., 32:6 (2022), 726–728
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