The stability and reactivity of activated acryloylcarbamates as reagents for the synthesis of N-1 substituted thymine and uracil - An NMR and DFT study
The mechanism of the decomposition of acryloylcarbamates 7a-b yielding highly reactive isocyanates 3a-b was proposed based on NMR measurements and quantum chemical calculations. A good agreement between the experimental kinetic data and DFT calculations allowed us to demonstrate that the stability of 7a-d depends on the presence of methyl in the acryloyl moiety and the position of the nitro group in the nitrophenolic part of the molecule. Furthermore, the reactivity of 7a-d with weakly nucleophilic and sterically hindered 2,4,6-tri-tert-butylaniline was explored by 1H NMR demonstrating the usefulness of reagents 7a-d offering access to a variety of 1-N-substituted uracils and thymines with potentially interesting biological properties. Copyright
A convenient, high-yield synthesis of 1-substituted uracil and thymine derivatives
Novel reagents for the synthesis of 1-substituted uracil and thymine derivatives have been developed. The aminolysis of 2- or 4-nitrophenyl 3-ethoxyacryloylcarbamate and 3-ethoxy-2-methylacryloylcarbamate with a variety of primary amino derivatives procee
Rejman, Dominik,Kova?ková, Soňa,Pohl, Radek,Dra?ínsky, Martin,Fiedler, Pavel,Rosenberg, Ivan
experimental part
p. 8513 - 8523
(2010/01/06)
More Articles about upstream products of 1271239-29-2