- Oxidation reactions of azines. 10. Synthesis, structure, and oxodihydroxylation of 3-hydroxymethyl-1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine
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It has been established that oxidation of a mixture of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine and dicyanomethane or formaldehyde with manganese dioxide gives 3-hydroxymethyl-1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine, the structure of which was confirmed by X-ray structural analysis. Some oxidative conversions by potassium permanganate of the product formed and its esters have been studied. These included lactamization, aromatization, and oxodihydroxylation.
- Soldatenkov,Temesgen,Polyanskii,Soldatova,Kolyadina,Golovtsov,Sergeeva
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p. 471 - 477
(2007/10/03)
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- Prins reaction under manganese dioxide control: The synthesis of 6-oxa-2-azabicyclo[3.2.1]octan-4-ones from tetrahydropyridines and formaldehyde
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The course of the acid-catalysed Prins reaction of tetrahydropyridines 1 with formaldehyde, leading to derivatives of piperidino-dioxane 4 and 3-oxa-7-azabicyclononanes 5 and 6, is dramatically changed in the presence of manganese dioxide to give new products, 6-oxa-2-azabicyclo[3.2.1]octan-4-ones 7 and 8.
- Soldatenkov,Polyanskii,Temesgen,Soldatova,Sergeeva,Kolyadina,Lobanov
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- Isolation and Structure Elucidation of the By-Product Formed in the Aminomethylation of α-Methylstyrene
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Aminomethylation of α-Methylstyrene (1) leads to 1,2,3,6-tetrahydro-4-phenylpyridine (3) as main product, together with a significant amount of a previously unknown by-product.The N-methyl, O-acetyl-N-methyl, N,O-diacetyl, N-(4-nitrobenzoyl), and (via N -> O acyl-migration) O-(4-nitrobenzoyl) derivatives of the by-product were synthesized.By aromatization of the heteroring, 4-phenyl-3-pyridinemethanol (8a) was obtained.According to these derivatives and their IR, 1H and 13C NMR spectra, the by-product is 1,2,3,6-tetrahydro-4-phenyl-3-pyridine-methanol (4a).
- Sohar, Pal,Lazar, Janos,Bernath, Gabor
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p. 551 - 559
(2007/10/02)
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