1 research outputs found
Mechanistic Investigation of the Reactions between Cyclohexane Carboxaldehyde and Ureido Groups
Model
reactions have been performed to explore the reactivity of
a variety of ureido groups with cyclohexane carboxaldehyde. The reaction
mechanism between ureido and aldehyde functionalities is more complicated
than expected. A new heterocyclic product was identified, which is
very stable and solvent resistant. The final product profile is reactant
and solvent dependent. In the cases of urea, alkyl urea, and benzyl
urea, the reaction pathway goes from hemiaminal to aminal, to enamine,
and finally to the heterocyclic product with nearly 100% yield. For
other investigated ureido groups, the reaction stopped at the enamine
product, and products are a mixture of hemiaminal, aminal, and enamine.
All reaction steps are reversible except for the last step. The structure
of the unique cyclic product was determined combining NMR and LC–MS
analysis, and the reaction pathway was verified by kinetics studies