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Mendeleev Communications, 2017, Volume 27, Issue 6, Pages 559–561
DOI: https://doi.org/10.1016/j.mencom.2017.11.006
(Mi mendc2058)
 

This article is cited in 18 scientific papers (total in 18 papers)

Communications

‘On-solvent’ new domino reaction of salicylaldehyde, malononitrile and 4-hydroxy-6-methylpyridin-2(1H)-one: fast and efficient approach to medicinally relevant 4-pyridinyl-2-amino-4H-chromene scaffold

M. N. Elinson, F. V. Ryzhkov, A. N. Vereshchagin, A. D. Korshunov, R. A. Novikov, M. P. Egorov

N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russian Federation
Abstract: Sodium acetate catalyzed assembling of salicylaldehydes, malononitrile and 4-hydroxy-6-methylpyridin-2(1H)-one in small amount of ethanol gives rapidly (5 min) substituted 4-pyridinyl-2-amino-4H-chromenes in 82–99% yields. This novel domino reaction opens the fast, facile, and flexible way to the new type of functionalized 2-amino-4H-chromene scaffold containing uracil-like moiety, which are relevant compounds for diverse biomedical applications.
Document Type: Article
Language: English
Supplementary materials:
Supplementary_data_1.pdf (903.9 Kb)


Citation: M. N. Elinson, F. V. Ryzhkov, A. N. Vereshchagin, A. D. Korshunov, R. A. Novikov, M. P. Egorov, “‘On-solvent’ new domino reaction of salicylaldehyde, malononitrile and 4-hydroxy-6-methylpyridin-2(1H)-one: fast and efficient approach to medicinally relevant 4-pyridinyl-2-amino-4H-chromene scaffold”, Mendeleev Commun., 27:6 (2017), 559–561
Linking options:
  • https://www.mathnet.ru/eng/mendc2058
  • https://www.mathnet.ru/eng/mendc/v27/i6/p559
  • This publication is cited in the following 18 articles:
    1. K. Nissi Sharon, P. Padmaja, P. Narayana Reddy, “A Brief Review on the Synthesis of 4H‐Chromene‐Embedded Heterocycles”, ChemistrySelect, 9:27 (2024)  crossref
    2. Ghodsi Mohammadi Ziarani, Mahdieh Khademi, Fatemeh Mohajer, Alireza Badiei, “The Application of Modified SBA-15 as a Chemosensor”, CNM, 7:1 (2022), 4  crossref
    3. Anatoly N. Vereshchagin, Taigib M. Iliyasov, Kirill A. Karpenko, Radmir N. Akchurin, Mikhail E. Minyaev, “Tetrahydropyridines' Stereoselective Formation, How Lockdown Assisted in the Identification of the Features of Its Mechanism”, Molecules, 27:14 (2022), 4367  crossref
    4. Fedor V. Ryzhkov, Michail N. Elinson, Yuliya E. Ryzhkova, Anatoly N. Vereshchagin, Alexander S. Goloveshkin, Mikhail P. Egorov, “Stereoselective domino assembling of five molecules: one-pot approach to (2 ′ R * ,3S * ,4 ′ R * )-2 ′ ,4 ′ -diaryl-1 ′ ,4 ′ -dihydro-2 ′ H-spiro[indoline-3,3 ′ -pyridines]”, Comptes Rendus. Chimie, 23:2 (2020), 159  crossref
    5. Michail N. Elinson, Anatoly N. Vereshchagin, Yuliya E. Anisina, Stepan K. Krymov, Artem N. Fakhrutdinov, Alexander S. Goloveshkin, Mikhail P. Egorov, “Pot, atom and step economic (PASE) assembly of salicylaldehydes, malononitrile dimer and 4-hydroxypyridine-2(1H)-ones into medicinally relevant 5H-chromeno[2,3-b]pyridine scaffold”, Mol Divers, 24:3 (2020), 617  crossref
    6. Nhlanhla Gracious Shabalala, Nagaraju Kerru, Suresh Maddila, Werner E. van Zyl, Sreekantha B. Jonnalagadda, “Catalyst-free synthesis of novel isopropyl 2-amino-7,7-dimethyl-4-(aryl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carboxylate derivatives in aqueous ethanol under ultrasound irradiation”, Chemical Data Collections, 26 (2020), 100365  crossref
    7. Alexey A. Festa, Olga A. Storozhenko, Nikita E. Golantsov, Karthikeyan Subramani, Roman A. Novikov, Snezhana O. Zaitseva, Mikhail S. Baranov, Alexey V. Varlamov, Leonid G. Voskressensky, “Homophtalonitrile for Multicomponent Reactions: Syntheses and Optical Properties of o‐Cyanophenyl‐ or Indol‐3‐yl‐Substituted Chromeno[2,3‐c]isoquinolin‐5‐Amines”, ChemistryOpen, 8:1 (2019), 23  crossref
    8. Michail N. Elinson, Anatoly N. Vereshchagin, Yuliya E. Anisina, Artem N. Fakhrutdinov, Alexander S. Goloveshkin, Mikhail P. Egorov, “Pot‐, Atom‐ and Step‐Economic (PASE) Multicomponent Approach to the 5‐(Dialkylphosphonate)‐Substituted 2,4‐Diamino‐5H‐chromeno[2,3‐b]pyridine Scaffold”, Eur J Org Chem, 2019:26 (2019), 4171  crossref
    9. Michail N. Elinson, Anatoly N. Vereshchagin, Yuliya E. Anisina, Stepan K. Krymov, Artem N. Fakhrutdinov, Mikhail P. Egorov, “Selective multicomponent 'one-pot' approach to the new 5-(4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)chromeno[2,3-b]pyridine scaffold in pyridine–ethanol catalyst/solvent system”, Monatsh Chem, 150:6 (2019), 1073  crossref
    10. Dmitry G. Kim, Elena V. Kalita, Vladimir V. Sharutin, Irina G. Ovchinnikova, Marina A. Ezhikova, Mikhail I. Kodess, Pavel A. Slepukhin, Anna V. Vasilenko, “Synthesis and halocyclization of 3-cyano-4,6-dimethyl-2-pyridone allyl derivatives”, Chem Heterocycl Comp, 55:6 (2019), 566  crossref
    11. I. G. Mamedov, V. N. Khrustalev, P. V. Dorovatovskii, F. N. Naghiev, A. M. Maharramov, “Efficient synthesis of new tricyclic pyrano[3,2-c]pyridine derivatives”, Mendeleev Commun., 29:2 (2019), 232–233  mathnet  crossref
    12. M. N. Elinson, A. N. Vereshchagin, Yu. E. Anisina, S. K. Krymov, A. N. Fakhrutdinov, M. P. Egorov, “Multicomponent assembling of salicylaldehydes, kojic acid and malonic acid derivatives”, Mendeleev Commun., 29:5 (2019), 581–583  mathnet  crossref
    13. M. N. Elinson, A. N. Vereshchagin, Y. E. Anisina, A. S. Goloveshkin, I. E. Ushakov, M. P. Egorov, “Multicomponent transformation of salicylaldehydes, 2-aminoprop-1-ene-1,1,3-tricarbonitrile, and pyrazolin-5-ones into substituted 2,4-diamino-5-(5-hydroxy-3-methyl-1H-pyrazol-4-yl)-5H-chromeno[2,3-b]pyridine-3-carbonitriles”, Russ Chem Bull, 67:9 (2018), 1695  crossref
    14. Michail N. Elinson, Anatoly N. Vereshchagin, Yuliya E. Anisina, Artem N. Fakhrutdinov, Alexander S. Goloveshkin, Mikhail P. Egorov, “A facile and efficient multicomponent approach to 5-[5-hydroxy- 3-(trifluoromethyl)-1H-pyrazol-4-yl]-5H-chromeno[2,3-b]pyridines”, Journal of Fluorine Chemistry, 213 (2018), 31  crossref
    15. A. N. Vereshchagin, K. A. Karpenko, M. N. Elinson, S. V. Gorbunov, Yu. E. Anisina, M. P. Egorov, “Stereoselective multicomponent synthesis of (2RS,6SR)-2,6-diaryl-3,3,5,5-tetracyanopiperidines”, Russ Chem Bull, 67:8 (2018), 1534  crossref
    16. A. N. Vereshchagin, K. A. Karpenko, T. M. Iliyasov, M. N. Elinson, E. O. Dorofeeva, A. N. Fakhrutdinov, M. P. Egorov, “Diastereoselective multicomponent synthesis of (4RS,6SR)-4,6-diaryl-5,5-dicyano-2-methyl-1,4,5,6-tetrahydropyridine-3-carboxylates”, Russ Chem Bull, 67:11 (2018), 2049  crossref
    17. A. N. Vereshchagin, K. A. Karpenko, M. N. Elinson, E. O. Dorofeeva, A. S. Goloveshkin, M. P. Egorov, “Pseudo six-component stereoselective synthesis of 2,4,6-triaryl-3,3,5,5-tetracyanopiperidines”, Mendeleev Commun., 28:4 (2018), 384–386  mathnet  crossref
    18. M. N. Elinson, A. N. Vereshchagin, Yu. E. Anisina, A. S. Goloveshkin, I. E. Ushakov, M. P. Egorov, “PASE facile and efficient multicomponent approach to the new type of 5-C-substituted 2,4-diamino-5H-chromeno[2,3-b]pyridine scaffold”, Mendeleev Commun., 28:4 (2018), 372–374  mathnet  crossref
    Citing articles in Google Scholar: Russian citations, English citations
    Related articles in Google Scholar: Russian articles, English articles
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