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Mendeleev Communications, 1997, Volume 7, Issue 6, Pages 243–244
DOI: https://doi.org/10.1070/MC1997v007n06ABEH000870
(Mi mendc4878)
 

This article is cited in 7 scientific papers (total in 7 papers)

New oxidative reactions of 1,2,3,6-tetrahydropyridines: imination, lactamination and decyclisation in the presence of potassium permanganate

A. T. Soldatenkov, V. V. Shereshovets, I. A. Bekro, T. P. Khristoforova, S. A. Soldatova, B. N. Anissimov

Peoples Friendship University of Russia (RUDN University), Moscow, Russian Federation
Full-text PDF (94 kB) Citations (7)
Abstract: A novel oxidative imination reaction of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine 1a by 4-nitroaniline/potassium permanganate has been found to occur yielding 2-(4-nitrophenyl)imino-1,2,5,6-tetrahydropyridine 4; in the absence of nitroaniline the shorter reaction time allows the reaction to be stopped at the unsaturated lactam 5 formation stage; the oxidation of 1a hydrochloride leads to 1-(N-formyl-N-methyl)amino-3-phenylpropan-2-one 6 via decyclisation–elimination steps, providing a new method for N-formyl-substituted aminoketone synthesis.
Document Type: Article
Language: English


Citation: A. T. Soldatenkov, V. V. Shereshovets, I. A. Bekro, T. P. Khristoforova, S. A. Soldatova, B. N. Anissimov, “New oxidative reactions of 1,2,3,6-tetrahydropyridines: imination, lactamination and decyclisation in the presence of potassium permanganate”, Mendeleev Commun., 7:6 (1997), 243–244
Linking options:
  • https://www.mathnet.ru/eng/mendc4878
  • https://www.mathnet.ru/eng/mendc/v7/i6/p243
  • This publication is cited in the following 7 articles:
    1. Omar Gómez-García, Héctor Salgado-Zamora, Elena Campos-Aldrete, “Tertiary formylated amines by microwave irradiation of N,N-dimethyl-N′-(2-pyridyl)formamidines with methyl vinyl ketone”, Heterocyclic Communications, 20:1 (2014), 21  crossref
    2. A. V. Malkova, V. E. Kotsyuba, A. T. Soldatenkov, S. A. Soldatova, K. B. Polyanskii, N. M. Kolyadina, V. N. Khrustalev, “Oxidation reactions of azines: XIII. Synthesis, molecular structure, and oxidation reactions of 3-methyl-3,3′,4,4′,5,6-hexahydro-1′H,2H-spiro[benzo[f]isoquinoline-1,2′-naphthalen]-1′-one”, Russ J Org Chem, 50:12 (2014), 1797  crossref
    3. A. T. Soldatenkov, K. B. Polyanskii, V. V. Shereshovets, S. A. Soldatova, N. D. Sergeeva, N. M. Kolyadina, N. N. Lobanov, “One-pot condensation of 2-arylpropenes with formaldehyde and ammonium chloride: the synthesis of aryl substituted pyridines and 5,7,11-trioxa-1-azatricyclo[7.3.1.03,8]tridecanes”, Mendeleev Commun., 11:4 (2001), 154–155  mathnet  crossref
    4. A. T. Soldatenkov, K. B. Polyanskii, V. V. Shereshovets, S. A. Soldatova, N. D. Sergeeva, N. M. Kolyadina, N. N. Lobanov, “Prins reaction under manganese dioxide control: the synthesis of 6-oxa-2-azabicyclo[3.2.1]octan-4-ones from tetrahydropyridines and formaldehyde”, Mendeleev Commun., 11:1 (2001), 27–29  mathnet  crossref
    5. A. T. SOLDATENKOV, A. W. TEMESGEN, I. A. BEKRO, T. P. KHRISTOFOROVA, S. A. SOLDATOVA, B. N. ANISSIMOV, “ChemInform Abstract: New Oxidative Reactions of 1,2,3,6‐Tetrahydropyridines: Imination, Lactamination and Decyclization in the Presence of Potassium Permanganate.”, ChemInform, 29:20 (1998)  crossref
    6. A. T. Soldatenkov, V. V. Shereshovets, L. N. Kuleshova, V. N. Khrustalev, “Oxidative coupling and unusual hydroxymethylation of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine in the presence of dicyanomethane”, Mendeleev Commun., 8:5 (1998), 193–195  mathnet  crossref
    7. A. T. Soldatenkov, V. V. Shereshovets, I. A. Bekro, S. A. Soldatova, B. N. Anissimov, “Cascade and stepwise oxidation of 4-phenyl- and 4-(γ-pyridyl)tetrahydropyridines”, Mendeleev Commun., 8:4 (1998), 137–138  mathnet  crossref
    Citing articles in Google Scholar: Russian citations, English citations
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