C-(4-[18F]fluorophenyl)-N-phenyl nitrone: A novel 18F-labeled building block for metal free [3+2]cycloaddition

B.D. Zlatopolskiy; R. Kandler; F.M. Mottaghy; B. Neumaier

doi:10.1016/j.apradiso.2011.09.002

C-(4-[18F]fluorophenyl)-N-phenyl nitrone: A novel 18F-labeled building block for metal free [3+2]cycloaddition

B.D. Zlatopolskiy, R. Kandler, F.M. Mottaghy, B. Neumaier^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › Academic › peer-review

Abstract

Radiofluorination via [3+2]-nitrone-alkene cycloaddition was studied using the model reaction between (18)F-labeled C-(4-fluorophenyl)-N-phenyl nitrone ([(18)F]1) and substituted maleimides 2a-c. [(18)F]1 was prepared in RCY of 73.6+/-5.8% and radiochemical purity of >95%. Cycloaddition of [(18)F]1 to 2a in toluene at 80 degrees C and in EtOH at 110 degrees C gave the respective isoxazolidine [(18)F]5a in >80% RCY at 10min reaction time. Reaction between [(18)F]1 and 2b, c also went smoothly to afford the respective cycloaddition products in high radiochemical yields.

Original language	English
Pages (from-to)	184-192
Journal	Applied Radiation and Isotopes
Volume	70
Issue number	1
DOIs	https://doi.org/10.1016/j.apradiso.2011.09.002
Publication status	Published - 1 Jan 2012

Access to Document

10.1016/j.apradiso.2011.09.002

Cite this

@article{224aacde1a0e405e9b852165ea363ad6,

title = "C-(4-[18F]fluorophenyl)-N-phenyl nitrone: A novel 18F-labeled building block for metal free [3+2]cycloaddition",

abstract = "Radiofluorination via [3+2]-nitrone-alkene cycloaddition was studied using the model reaction between (18)F-labeled C-(4-fluorophenyl)-N-phenyl nitrone ([(18)F]1) and substituted maleimides 2a-c. [(18)F]1 was prepared in RCY of 73.6+/-5.8% and radiochemical purity of >95%. Cycloaddition of [(18)F]1 to 2a in toluene at 80 degrees C and in EtOH at 110 degrees C gave the respective isoxazolidine [(18)F]5a in >80% RCY at 10min reaction time. Reaction between [(18)F]1 and 2b, c also went smoothly to afford the respective cycloaddition products in high radiochemical yields.",

author = "B.D. Zlatopolskiy and R. Kandler and F.M. Mottaghy and B. Neumaier",

year = "2012",

month = jan,

day = "1",

doi = "10.1016/j.apradiso.2011.09.002",

language = "English",

volume = "70",

pages = "184--192",

journal = "Applied Radiation and Isotopes",

issn = "0969-8043",

publisher = "Elsevier Limited",

number = "1",

}

TY - JOUR

T1 - C-(4-[18F]fluorophenyl)-N-phenyl nitrone: A novel 18F-labeled building block for metal free [3+2]cycloaddition

AU - Zlatopolskiy, B.D.

AU - Kandler, R.

AU - Mottaghy, F.M.

AU - Neumaier, B.

PY - 2012/1/1

Y1 - 2012/1/1

N2 - Radiofluorination via [3+2]-nitrone-alkene cycloaddition was studied using the model reaction between (18)F-labeled C-(4-fluorophenyl)-N-phenyl nitrone ([(18)F]1) and substituted maleimides 2a-c. [(18)F]1 was prepared in RCY of 73.6+/-5.8% and radiochemical purity of >95%. Cycloaddition of [(18)F]1 to 2a in toluene at 80 degrees C and in EtOH at 110 degrees C gave the respective isoxazolidine [(18)F]5a in >80% RCY at 10min reaction time. Reaction between [(18)F]1 and 2b, c also went smoothly to afford the respective cycloaddition products in high radiochemical yields.

AB - Radiofluorination via [3+2]-nitrone-alkene cycloaddition was studied using the model reaction between (18)F-labeled C-(4-fluorophenyl)-N-phenyl nitrone ([(18)F]1) and substituted maleimides 2a-c. [(18)F]1 was prepared in RCY of 73.6+/-5.8% and radiochemical purity of >95%. Cycloaddition of [(18)F]1 to 2a in toluene at 80 degrees C and in EtOH at 110 degrees C gave the respective isoxazolidine [(18)F]5a in >80% RCY at 10min reaction time. Reaction between [(18)F]1 and 2b, c also went smoothly to afford the respective cycloaddition products in high radiochemical yields.

U2 - 10.1016/j.apradiso.2011.09.002

DO - 10.1016/j.apradiso.2011.09.002

M3 - Article

C2 - 21945016

SN - 0969-8043

VL - 70

SP - 184

EP - 192

JO - Applied Radiation and Isotopes

JF - Applied Radiation and Isotopes

IS - 1

ER -