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Mendeleev Communications, 2016, Volume 26, Issue 5, Pages 399–401
DOI: https://doi.org/10.1016/j.mencom.2016.09.011
(Mi mendc2226)
 

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

Communications

Multicomponent assembling of isatins, malononitrile and 4-hydroxy-6-methylpyridin-2(1H)-ones: one-pot efficient approach to privileged spiro[indoline-3,4-pyrano[3,2-c]pyridine]-2,5(6’H)-dione scaffold

M. N. Elinsona, F. V. Ryzhkova, A. N. Vereshchagina, T. A. Zaimovskayab, V. A. Koroleva, M. P. Egorova

a N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russian Federation
b A.V. Topchiev Institute of Petrochemical Synthesis, Russian Academy of Sciences, Moscow, Russian Federation
Abstract: The new one-pot multicomponent assembling of isatins, malononitrile and 4 hydroxy-6-methylpyridin-2(1H)-ones into previously unknown 2-amino-7-methyl-2,5-dioxo-5,6-dihydrospiro[indoline-3,4-pyrano[3,2-c]pyridine]-3-carbonitriles in 80–98% yields has been accomplished by their reflux in ethanol in the presence of sodium acetate.
Document Type: Article
Language: English
Supplementary materials:
Supplementary_data_1.pdf (229.0 Kb)


Citation: M. N. Elinson, F. V. Ryzhkov, A. N. Vereshchagin, T. A. Zaimovskaya, V. A. Korolev, M. P. Egorov, “Multicomponent assembling of isatins, malononitrile and 4-hydroxy-6-methylpyridin-2(1H)-ones: one-pot efficient approach to privileged spiro[indoline-3,4-pyrano[3,2-c]pyridine]-2,5(6’H)-dione scaffold”, Mendeleev Commun., 26:5 (2016), 399–401
Linking options:
  • https://www.mathnet.ru/eng/mendc2226
  • https://www.mathnet.ru/eng/mendc/v26/i5/p399
  • This publication is cited in the following 18 articles:
    1. Fatemeh Asilpour, Dariush Saberi, Alireza Hasaninejad, “Synthesis of novel chromeno[1,6]naphthyridine derivatives in PEG-400 via catalyst-free, one-pot, and multicomponent reactions”, New J. Chem., 48:1 (2024), 237  crossref
    2. Michail N. Elinson, Anatoly N. Vereshchagin, Yuliya E. Ryzhkova, Kirill A. Karpenko, Varvara M. Kalashnikova, “Cascade assembling of aldehydes and two molecules of dimedone into 4H-spiro[1-benzofuran-2,1'-cyclohexane]-2',4,6'-triones under column chromatography-free protocol at room temperature”, Chem Heterocycl Comp, 60:5-6 (2024), 239  crossref
    3. Dipti B. Upadhyay, Ruturajsinh M. Vala, Subham G. Patel, Paras J. Patel, Celestine Chi, Hitendra M. Patel, “Water mediated TBAB catalyzed synthesis of spiro-indoline-pyrano[3,2-c]quinolines as α-amylase inhibitor and in silico studies”, Journal of Molecular Structure, 1273 (2023), 134305  crossref
    4. Nawel Mehiaoui, Ridha Hassaine, Amina Berrichi, Zahira Kibou, Noureddine Choukchou-Braham, “Synthesis of Highly Heterocyclic Fluorescent Molecules: 2-imino-2H-pyrano[3,2-c] Pyridin-5(6H)-ones Derivatives”, J Fluoresc, 33:5 (2023), 1995  crossref
    5. Yuliya E. Ryzhkova, Varvara M. Kalashnikova, Michail N. Elinson, “6′-Amino-5,7-dibromo-2-oxo-3′-(trifluoromethyl)-1′H-spiro[indoline-3,4′-pyrano[2,3-c]pyrazole]-5′-carbonitrile”, Molbank, 2022:1 (2021), M1309  crossref
    6. Pedro Brandão, Carolina S. Marques, Elisabete P. Carreiro, M. Pineiro, Anthony J. Burke, “Engaging Isatins in Multicomponent Reactions (MCRs) – Easy Access to Structural Diversity”, The Chemical Record, 21:4 (2021), 924  crossref
    7. Majid Heravi, Vahideh Zadsirjan, Recent Advances in Applications of Name Reactions in Multicomponent Reactions, 2020, 139  crossref
    8. Majid Heravi, Vahideh Zadsirjan, Recent Advances in Applications of Name Reactions in Multicomponent Reactions, 2020, 269  crossref
    9. I. G. Mamedov, F. N. Naghiev, A. M. Maharramov, O. Uwangue, A. Farewell, P. Sunnerhagen, M. Erdelyi, “Antibacterial activity of 2-amino-3-cyanopyridine derivatives”, Mendeleev Commun., 30:4 (2020), 498–499  mathnet  crossref
    10. Zhenhang Xu, Yijun Du, Songxiang Wang, Zeru Wu, Yuhao Lou, Furen Zhang, “One‐pot Two‐step Reaction for Synthesis of Poly‐substituted Pyrano[3,2‐c]pyridones and Spiro[indoline‐3,4′‐pyrano[3,2‐c]pyridine]‐2,5′(6′H)‐diones in Water”, Journal of Heterocyclic Chem, 56:9 (2019), 2517  crossref
    11. 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
    12. 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
    13. 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
    14. Vairaperumal Veeramani, Perumal Muthuraja, Sengodu Prakash, Muthiah Senthil Kumar, Antony Susaimanickam, Paramasivam Manisankar, “NbCl5‐Catalyzed One‐Pot Four Component Synthesis of Spiro Pyrazole and Benzo[7, 8]chromene Derivatives”, ChemistrySelect, 3:35 (2018), 10027  crossref
    15. D. A. Tatarinov, V. I. Osipova, A. V. Bogdanov, R. R. Fayzullin, V. F. Mironov, “3-(4-Phosphoryl-4-methyl-2-oxopentyl)-3-hydroxyindolin-2-ones, the first phosphorus analogues of natural convolutamydines”, Mendeleev Commun., 28:3 (2018), 292–294  mathnet  crossref
    16. 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
    17. 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
    18. A. N. Vereshchagin, “Classical and interdisciplinary approaches to the design of organic and hybrid molecular systems”, Russ Chem Bull, 66:10 (2017), 1765  crossref
    Citing articles in Google Scholar: Russian citations, English citations
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