Abstract:
5,7-Dimethoxy-8-(3,6-diphenylpyridin-2-yl)coumarins were obtained from 5,7-dimethoxycoumarins and 3,6-diphenyl-1,2,4-triazines via the protocol comprising aromatic
SHNSHN
substitution in the triazine ring followed by the Boger transformation of formed triazine moiety into the pyridine one. The advantages of the suggested method are simple procedures, high yields, and the absence of transition-metal catalysts.
Citation:
R. F. Fatykhov, M. I. Savchuk, E. S. Starnovskaya, M. V. Bobkina, D. S. Kopchuk, E. V. Nosova, G. V. Zyryanov, I. A. Khalymbadzha, O. N. Chupakhin, V. N. Charushin, V. G. Kartsev, “Nucleophilic substitution of hydrogen–the Boger reaction sequence as an approach towards 8-(pyridin-2-yl)coumarins”, Mendeleev Commun., 29:3 (2019), 299–300
\Bibitem{FatSavSta19}
\by R.~F.~Fatykhov, M.~I.~Savchuk, E.~S.~Starnovskaya, M.~V.~Bobkina, D.~S.~Kopchuk, E.~V.~Nosova, G.~V.~Zyryanov, I.~A.~Khalymbadzha, O.~N.~Chupakhin, V.~N.~Charushin, V.~G.~Kartsev
\paper Nucleophilic substitution of hydrogen–the Boger reaction sequence as an approach towards 8-(pyridin-2-yl)coumarins
\jour Mendeleev Commun.
\yr 2019
\vol 29
\issue 3
\pages 299--300
\mathnet{http://mi.mathnet.ru/mendc1502}
\crossref{https://doi.org/10.1016/j.mencom.2019.05.019}
Linking options:
https://www.mathnet.ru/eng/mendc1502
https://www.mathnet.ru/eng/mendc/v29/i3/p299
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P. A. Slepukhin, R. F. Fatykhov, A. D. Sharapov, M. I. Valieva, E. S. Starnovskaya, I. A. Khalymbadzha, D. S. Kopchuk, G. V. Zyryanov, O. N. Chupakhin, “X-Ray Diffraction Study of 8-(Pyridin-2-yl)- and 8-(1,2,4-Triazin-5-yl)-2H-chromen-2-ones”, Russ J Gen Chem, 92:7 (2022), 1285
S.M. Ivanov, Comprehensive Heterocyclic Chemistry IV, 2022, 29
Ramil F. Fatykhov, Igor A. Khalymbadzha, Ainur D. Sharapov, Anastasia P. Potapova, Nataliya N. Mochulskaya, Anton N. Tsmokalyuk, Alexandra V. Ivoilova, Polina N. Mozharovskaia, Sougata Santra, Oleg N. Chupakhin, “MnO2-Mediated Oxidative Cyclization of “Formal” Schiff's Bases: Easy Access to Diverse Naphthofuro-Annulated Triazines”, Molecules, 27:20 (2022), 7105
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Ramil F. Fatykhov, Ainur D. Sharapov, Ekaterina S. Starnovskaya, Yaroslav K. Shtaitz, Maria I. Savchuk, Dmitry S. Kopchuk, Igor L. Nikonov, Grigory V. Zyryanov, Igor A. Khalymbadzha, Oleg N. Chupakhin, “Coumarin-pyridine push-pull fluorophores: Synthesis and photophysical studies”, Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 267 (2022), 120499
A. P. Krinochkin, E. S. Starnovskaya, M. I. Valieva, D. S. Kopchuk, S. Santra, P. A. Slepukhin, G. V. Zyryanov, A. Majee, O. N. Chupakhin, “One-pot synthesis of cyclopentane-fused 5'-aryl-4-cycloalkylamino-2,2'-bipyridines via the aza-Diels–Alder/SNipso reactions”, Mendeleev Commun., 32:4 (2022), 449–451
Maria I. Savchuk, Dmitry S. Kopchuk, Olga S. Taniya, Igor L. Nikonov, Ilya N. Egorov, Sougata Santra, Grigory V. Zyryanov, Oleg N. Chupakhin, Valery N. Charushin, “5-Aryl-6-arylthio-2,2′-bipyridine and 6-Arylthio-2,5-diarylpyridine Fluorophores: Pot, Atom, Step Economic (PASE) Synthesis and Photophysical Studies”, J Fluoresc, 31:4 (2021), 1099
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R. Chatterjee, A. Mukherjee, S. Santra, G. V. Zyryanov, O. N. Chupakhin, A. Majee, “An expedient solvent-free C-benzylation of 4-hydroxycoumarin with styrenes”, Mendeleev Commun., 31:1 (2021), 123–124
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Ramil F. Fatykhov, Igor A. Khalymbadzha, Vladimir L. Rusinov, Oleg N. Chupakhin, PROCEEDINGS OF INTERNATIONAL CONFERENCE ON RECENT TRENDS IN MECHANICAL AND MATERIALS ENGINEERING: ICRTMME 2019, 2283, PROCEEDINGS OF INTERNATIONAL CONFERENCE ON RECENT TRENDS IN MECHANICAL AND MATERIALS ENGINEERING: ICRTMME 2019, 2020, 040015
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