94515-22-7Relevant academic research and scientific papers
Oxidizing reactions of azines. 7*. Imination of 4-aryl-1,2,3,6-tetrahydropyridines by arylamines in the presence of potassium permanganate. Molecular structure of 1-methyl-2-(4-nitrophenylimino)-4-phenyl-1,2,5,6-tetrahydropyridine
Soldatenkov,Khristoforova,Temesgen,Anissimov,Averkiev,Kuleshova,Khrustalev,Antipin
, p. 715 - 722 (2001)
On treating 4-aryl substituted 1-methyl-1,2,3,6-tetrahydropyridines with potassium permanganate in the presence of arylamines a previously unknown intermolecular oxidative imination reaction occurs leading to the formation of 2-(arylimino)-1,2,5,6-tetrahydropyridines. The molecular structure of 1-methyl-2-(4-nitrophenylimino)-4-phenyl-1,2,5,6-tetrahydropyridine was studied by X-ray analysis and it was shown that the hydropyridine ring of the molecule has a sofa conformation and its amidine fragment is in the E-configuration.
Oxidative reactions of azines. 6. Lactamization of 4-aryl- and 4-phenethenyl-substituted 1,2,3,6-tetrahydropyridines and dihydroxylation of 4-aryl-1,2,5,6-tetrahydropyrid-2-ones using potassium permanganate
Soldatenkov,Temesgen,Bekro,Soldatova,Golovtsov,Sergeeva
, p. 1426 - 1430 (2007/10/03)
Oxidation of 4-phenyl-, 4-(4-pyridyl)-, and 4-phenethenyl-1,2,3,6-tetrahydropyridines with potassium permanganate can stop at the stage of the introduction of an oxo group into the allyl C(2) position of the piperideine fragment. In contrast to
Selective reductions of 1-methyl-4-phenyl-2-pyridone
Mabic,Castagnoli Jr.
, p. 309 - 313 (2007/10/03)
We have explored the reactions of 1-methyl-4-phenyl-2-pyridone (5) with various reducing agents in an effort to develop synthetic approaches to specifically deuterium-labeled 1,4-disubstituted 1,2,3,6-tetrahydropyridine analogs needed for metabolic and enzyme mechanistic studies. Reactions with NaBH4 in CH3OH or THF, LiAl(O-t-Bu)3H in THF, and Al(i-Bu)2H (DIBALH) in THF resulted in quantitative recovery of starting material. On the other hand, treatment with BH3 in THF unexpectedly led to the formation of 4-phenylpyridine (7) in 98% yield. LiAlH4 in THF or Et2O and Red-Al in THF gave varying amounts of the 3,6-dihydro-2-pyridone 8 and 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (1). In the presence of TiCl3, LiAlH4 in THF at 0°C converted 5 to 1 in 97% yield. LiB(s-Bu)3H (L-Selectride) in THF gave exclusively the 1,4-reduction product 8. Base catalyzed isomerization of 8 provided the conjugated 5,6-dihydro-2-pyridone 4. The applications of these reactions with deuterated reagents provide insights into the reaction pathways and several avenues for the regioselective synthesis of the required deuterium-labeled compounds.
