110864-92-1Relevant articles and documents
The stability and reactivity of activated acryloylcarbamates as reagents for the synthesis of N-1 substituted thymine and uracil - An NMR and DFT study
Pohl, Radek,Rulisek, Lubomir,Rejman, Dominik
supporting information; scheme or table, p. 423 - 430 (2011/11/14)
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
