Oxidative reactions of azines 5.* ketodihydroxylation and coupling of 4-(γ-pyridyl)-1,2,5,6-tetrahydropyridines with acetone. Molecular and crystal structure of 3,4-dihydroxy-4-(γ-pyridyl)-1-ethylpiperidin-2-one

Oxidative coupling of 1-alkyl(benzyl)-4-(γ-pyridyl)-1,2,5,6-tetrahydropyridines with acetone in the presence of KMnO4 follows two pathways and yields both 1-R-2-(acetylmethylene)tetrahydropyridines and 1-R-3,4-dihydroxypiperidin-2-ones. When acetonitrile is used instead of acetone, the reaction under similar conditions occurs as selective ketodihydroxylation of the starting piperideines yielding 1-R-3,4-dihydroxy-4-(γ-pyridyl)piperidin-2-ones. The molecular and crystal structures of one of these products (R = Et) was studied by X-ray diffraction analysis.

Authors
Editors
-
Publisher
-
Number of issue
11
Language
English
Pages
1916-1919
Status
Published
Department
-
Number
-
Volume
46
Year
1997
Organizations
  • 1 Russ. Peoples' Friendship University, 6 ul. Mikluho-Maklaya, 117198 Moscow, Russian Federation
  • 2 A. N. Nesmeyanov Inst. O., Russian Academy of Sciences, 28 ul. Vavilova, 117813 Moscow, Russian Federation
Keywords
NMR, X-ray diffraction analysis; Oxidative coupling, ketodihydroxylation, 1-R-4-(γ-pyridyl)-1,2,5,6-tetrahydropyridines, 1-R-3,4-dihydroxy-4-(γ-pyridyl)piperidin-2-ones, 1-R-2-acetylmethylene-4-(γ-pyridyl)-1,2,5,6-tetrahydropyridines
Date of creation
19.10.2018
Date of change
19.10.2018
Short link
https://repository.rudn.ru/en/records/article/record/772/