Home / Publications / Synthesis of diethyl (aryl)(4-oxopiperidin-1-yl)methylphosphonates

Synthesis of diethyl (aryl)(4-oxopiperidin-1-yl)methylphosphonates

3
Share
Cite this
GOST
 | 
Cite this
GOST Copy
Makarov M. V., Skvortsov E. A., Brel V. K. Synthesis of diethyl (aryl)(4-oxopiperidin-1-yl)methylphosphonates // Mendeleev Communications. 2015. Vol. 25. No. 3. pp. 232-233.
GOST all authors (up to 50) Copy
Makarov M. V., Skvortsov E. A., Brel V. K. Synthesis of diethyl (aryl)(4-oxopiperidin-1-yl)methylphosphonates // Mendeleev Communications. 2015. Vol. 25. No. 3. pp. 232-233.
RIS
 | 
Cite this
RIS Copy
TY - JOUR
DO - 10.1016/j.mencom.2015.05.026
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2015.05.026
TI - Synthesis of diethyl (aryl)(4-oxopiperidin-1-yl)methylphosphonates
T2 - Mendeleev Communications
AU - Makarov, Mikhail Viktorovich
AU - Skvortsov, Evgenii A
AU - Brel, Valery Kuzmich
PY - 2015
DA - 2015/04/28
PB - Mendeleev Communications
SP - 232-233
IS - 3
VL - 25
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors) Copy
@article{2015_Makarov,
author = {Mikhail Viktorovich Makarov and Evgenii A Skvortsov and Valery Kuzmich Brel},
title = {Synthesis of diethyl (aryl)(4-oxopiperidin-1-yl)methylphosphonates},
journal = {Mendeleev Communications},
year = {2015},
volume = {25},
publisher = {Mendeleev Communications},
month = {Apr},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2015.05.026},
number = {3},
pages = {232--233},
doi = {10.1016/j.mencom.2015.05.026}
}
MLA
Cite this
MLA Copy
Makarov, Mikhail Viktorovich, et al. “Synthesis of diethyl (aryl)(4-oxopiperidin-1-yl)methylphosphonates.” Mendeleev Communications, vol. 25, no. 3, Apr. 2015, pp. 232-233. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2015.05.026.

Abstract

The Kabachnik–Fields reaction of 4-piperidone hydrochloride monohydrate, an aromatic aldehyde and triethyl phosphite in the presence of triethylamine and magnesium perchlorate affords diethyl (aryl)(4-oxopiperidin-1-yl)methylphosphonates in moderate yields.

References

1.
Piperidin-4-one: The Potential Pharmacophore
Kant Sahu S., Kumar Dubey B., C. Tripathi A., Koshy M., K. Saraf S.
Mini-Reviews in Medicinal Chemistry, 2013
2.
Neuropharmacological activity of piperidine derivatives (a review)
Kurbat N.M., Praliev K.D., Salita T.A., Yu V.K., Verina E.L.
Pharmaceutical Chemistry Journal, 1991
4.
Prodrugs of phosphates, phosphonates, and phosphinates
Krise J.P., Stella V.J.
Advanced Drug Delivery Reviews, 1996
5.
Prodrugs of Phosphates and Phosphonates
Hecker S.J., Erion M.D.
Journal of Medicinal Chemistry, 2008
6.
Prodrugs - An Efficient Way to Breach Delivery and Targeting Barriers
M. Huttunen K., Rautio J.
Current Topics in Medicinal Chemistry, 2011
7.
1-Aminoalkylphosphonous acids. Part 1. Isosteres of the protein amino acids
Baylis E.K., Campbell C.D., Dingwall J.G.
Journal of the Chemical Society Perkin Transactions 1, 1984
8.
10.1016/j.mencom.2015.05.026_sbref0025b
Kafarski
Elem., 1991
9.
Remarkable Potential of the α-Aminophosphonate/Phosphinate Structural Motif in Medicinal Chemistry
10.
Design, cytotoxic and fluorescent properties of novel N-phosphorylalkyl substituted E,E-3,5-bis(arylidene)piperid-4-ones
Makarov M.V., Rybalkina E.Y., Röschenthaler G., Short K.W., Timofeeva T.V., Odinets I.L.
European Journal of Medicinal Chemistry, 2009
11.
(a) M. I. Kabachnik and T. Ya. Medved, Dokl. Akad. Nauk SSSR, 1952, 83, 689 (Chem. Abstr., 1953, 47, 2724b); (b) E. K. Fields, J. Am. Chem. Soc., 1952, 74, 1528.
15.
Organocatalytic synthesis of α-hydroxy and α-aminophosphonates
Vahdat S.M., Baharfar R., Tajbakhsh M., Heydari A., Baghbanian S.M., Khaksar S.
Tetrahedron Letters, 2008
16.
10.1016/j.mencom.2015.05.026_sbref0055b
Tajbakhsh
Synthesis, 2008
17.
An efficient and simple synthesis of α-amino phosphonates as ‘drug like’ molecules catalyzed by silica-supported perchloric acid (HClO4–SiO2)
Maghsoodlou M.T., Habibi-Khorassani S.M., Heydari R., Hazeri N., Sajadikhah S.S., Rostamizadeh M.
Arabian Journal of Chemistry, 2011