Home / Publications / Prins reaction under manganese dioxide control: the synthesis of 6-oxa-2-azabicyclo[3.2.1]octan-4-ones from tetrahydropyridines and formaldehyde

Prins reaction under manganese dioxide control: the synthesis of 6-oxa-2-azabicyclo[3.2.1]octan-4-ones from tetrahydropyridines and formaldehyde

Anatoly Timofeevich Soldatenkov 1
Anatoly Timofeevich Soldatenkov
, 
Kirill Borisovich Polyanskii 1
Kirill Borisovich Polyanskii
, 
Valerii Vladimirovich Shereshovets 1
Valerii Vladimirovich Shereshovets
, 
Svetlana Aleksandrovna Soldatova 1
Svetlana Aleksandrovna Soldatova
, 
Nataliya Dmitrievna Sergeeva 1
Nataliya Dmitrievna Sergeeva
, 
Nadezhda Mikhailovna Kolyadina 1
Nadezhda Mikhailovna Kolyadina
, 
10.1070/MC2001v011n01ABEH001386
Published 2001-02-22
Communication , Volume 11, Issue 1, 27-29
6
Share
Cite this
GOST
 | 
Cite this
GOST Copy
Soldatenkov A. T. et al. Prins reaction under manganese dioxide control: the synthesis of 6-oxa-2-azabicyclo[3.2.1]octan-4-ones from tetrahydropyridines and formaldehyde // Mendeleev Communications. 2001. Vol. 11. No. 1. pp. 27-29.
GOST all authors (up to 50) Copy
Soldatenkov A. T., Polyanskii K. B., Shereshovets V. V., Soldatova S. A., Sergeeva N. D., Kolyadina N. M., Lobanov N. N. Prins reaction under manganese dioxide control: the synthesis of 6-oxa-2-azabicyclo[3.2.1]octan-4-ones from tetrahydropyridines and formaldehyde // Mendeleev Communications. 2001. Vol. 11. No. 1. pp. 27-29.
RIS
 | 
Cite this
RIS Copy
TY - JOUR
DO - 10.1070/MC2001v011n01ABEH001386
UR - https://mendcomm.colab.ws/publications/10.1070/MC2001v011n01ABEH001386
TI - Prins reaction under manganese dioxide control: the synthesis of 6-oxa-2-azabicyclo[3.2.1]octan-4-ones from tetrahydropyridines and formaldehyde
T2 - Mendeleev Communications
AU - Soldatenkov, Anatoly Timofeevich
AU - Polyanskii, Kirill Borisovich
AU - Shereshovets, Valerii Vladimirovich
AU - Soldatova, Svetlana Aleksandrovna
AU - Sergeeva, Nataliya Dmitrievna
AU - Kolyadina, Nadezhda Mikhailovna
AU - Lobanov, Nikolai Nikolaevich
PY - 2001
DA - 2001/02/22
PB - Mendeleev Communications
SP - 27-29
IS - 1
VL - 11
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors) Copy
@article{2001_Soldatenkov,
author = {Anatoly Timofeevich Soldatenkov and Kirill Borisovich Polyanskii and Valerii Vladimirovich Shereshovets and Svetlana Aleksandrovna Soldatova and Nataliya Dmitrievna Sergeeva and Nadezhda Mikhailovna Kolyadina and Nikolai Nikolaevich Lobanov},
title = {Prins reaction under manganese dioxide control: the synthesis of 6-oxa-2-azabicyclo[3.2.1]octan-4-ones from tetrahydropyridines and formaldehyde},
journal = {Mendeleev Communications},
year = {2001},
volume = {11},
publisher = {Mendeleev Communications},
month = {Feb},
url = {https://mendcomm.colab.ws/publications/10.1070/MC2001v011n01ABEH001386},
number = {1},
pages = {27--29},
doi = {10.1070/MC2001v011n01ABEH001386}
}
MLA
Cite this
MLA Copy
Soldatenkov, Anatoly Timofeevich, et al. “Prins reaction under manganese dioxide control: the synthesis of 6-oxa-2-azabicyclo[3.2.1]octan-4-ones from tetrahydropyridines and formaldehyde.” Mendeleev Communications, vol. 11, no. 1, Feb. 2001, pp. 27-29. https://mendcomm.colab.ws/publications/10.1070/MC2001v011n01ABEH001386.

Abstract

The course of the acid-catalysed Prins reaction of tetrahydropyridines 1 with formaldehyde, leading to derivatives of piperidinodioxane 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.

References

1.
Notes - The Preparation of 4-Amino-2-phenyl-2-butanol
Mansfield R., Schmidle C.
Journal of Organic Chemistry, 1956
2.
4-Phenyl-1,2,3,6-tetrahydropyridines in the Prins reaction. Examples of a cis steric course
Casy A.F., Simmonds A.B., Staniforth D.
Journal of Organic Chemistry, 1972
4.
Soldatenkov A.T., Temesgen A.W., Bekro I.A., Khristoforova T.P., Soldatova S.A., Anissimov B.N.
Mendeleev Communications, 1997
5.
Soldatenkov A.T., Temesgen A.W., Bekro I.A., Soldatova S.A., Anissimov B.N.
Mendeleev Communications, 1998
7.
OXIDATION OF ORGANIC COMPOUNDS WITH ACTIVE MANGANESE DIOXIDE
Korshunov S.P., Vereshchagin L.I.
Russian Chemical Reviews, 1966
8.
10.1070/MC2001v011n01ABEH001386_bib8
Chichibabin
Zh. Russ. Fiz. -Khim. Obshch., 1930