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:
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
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
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
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
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)
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
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
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