TY - JOUR

T1 - Synthesis of allyloxycarbonyloxymethyl-5-fluorouracil and copolymerizations with N-vinylpyrrolidinone.

AU - Liu, Zuifang

AU - Fullwood, Nigel J.

AU - Rimmer, Steve

PY - 2000

Y1 - 2000

N2 - Poly(N-vinylpyrrolidinone)(PNVP) bearing 5-fluorouracil (5-FU) moieties was synthesised via a three-step method. Firstly, 5-FU reacted with formaldehyde to form a mixture of mono- and disubstituted hydroxymethyl-5-FUs. The mixture was then treated with allyl chloroformate to afford allyloxycarbonyloxymethyl-5-FUs. This reaction showed site-specificity: the hydroxymethyl goup at the N-1 position readily reacted with chloroformate whereas the N-3 hydroxymethyl group partially decomposed into formaldehyde and the amide group. 1-Allyloxycarbonyloxymethyl-5-FU ( 4) and NVP were copolymerized in dioxane using azobisisobutyronitrile as an initiator. The monomer reactivity ratios, r 4= 0.32 and rNVP= 0.97, were evaluated by both linear and non-linear methods.

AB - Poly(N-vinylpyrrolidinone)(PNVP) bearing 5-fluorouracil (5-FU) moieties was synthesised via a three-step method. Firstly, 5-FU reacted with formaldehyde to form a mixture of mono- and disubstituted hydroxymethyl-5-FUs. The mixture was then treated with allyl chloroformate to afford allyloxycarbonyloxymethyl-5-FUs. This reaction showed site-specificity: the hydroxymethyl goup at the N-1 position readily reacted with chloroformate whereas the N-3 hydroxymethyl group partially decomposed into formaldehyde and the amide group. 1-Allyloxycarbonyloxymethyl-5-FU ( 4) and NVP were copolymerized in dioxane using azobisisobutyronitrile as an initiator. The monomer reactivity ratios, r 4= 0.32 and rNVP= 0.97, were evaluated by both linear and non-linear methods.

U2 - 10.1039/b002092n

DO - 10.1039/b002092n

M3 - Journal article

VL - 10

SP - 1771

EP - 1775

JO - Journal of Materials Chemistry

JF - Journal of Materials Chemistry

SN - 0959-9428

IS - 8

ER -