Efficient Synthesis of Diethyl, Dialkyl a-Hydroxy-propylenebis- phosphonates and Related 5-Phosphonoyl-1,2-oxaphospholane 2-Oxides

A series of new dialkyl alpha-diethylphosphonoylethyl-alpha-hydroxy-ethylphosphonates were prepared using the Pudovik reaction of the corresponding gamma-oxophosphonate with dialkyl phosphites performed on the surface of Al2O3/KF. The adducts revealed unexpected reactivity in the attempted O-acylati...

Full description

Saved in:
Bibliographic Details
Published inSynthesis (Stuttgart) Vol. 56; no. 4; pp. 561 - 566
Main Authors Varga, Petra Regina, Belovics, Alexandra, Karaghiosoff, Konstantin, Szabo, Rita, Bosze, Szilvia, Drahos, Laszlo, Keglevich, Gyoergy
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 01.02.2024
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ACID
anticancer effect
ANTIBACTERIAL
CONVENIENT
PHOSPHITE
Pudovik reaction
cyclization
FLUORIDE
a-hydroxy-propyl-enebisphosphonate
ALPHA-HYDROXYPHOSPHONATES
y-oxophosphonate
ESTERS
POTASSIUM
DERIVATIVES
phosphonoyl-1
2-oxaphospholane 2-oxide
SOLVENT-FREE SYNTHESIS
Online AccessGet more information

Cover

More Information
Summary:A series of new dialkyl alpha-diethylphosphonoylethyl-alpha-hydroxy-ethylphosphonates were prepared using the Pudovik reaction of the corresponding gamma-oxophosphonate with dialkyl phosphites performed on the surface of Al2O3/KF. The adducts revealed unexpected reactivity in the attempted O-acylation reaction, and provided the corresponding 5-phosphonoyl-1,2-oxaphospholane 2-oxides. On treatment with Cs2CO3, instead of the expected rearrangement a cyclization reaction leading to the same ring products took place. Three of the phosphonoylethyl-alpha hydroxy-ethylphosphonates, along with two phosphonoylmethyl analogues revealed significant and selective anticancer effect on A431 cells, and occasionally, on PC-3 and MDA-MB 231 cells.
ISSN:0039-7881
1437-210X
DOI:10.1055/a-2122-4178