Pyrrolo[2,3-d]pyrimidine synthesis through activation of N-benzyl groups by distal amides.
A new activation mode of CH2-benzylamino groups has been observed during the preparation of pyrrolopyrimidines from Ugi-Smiles adducts of hydroxypyrimidines. The cyclization proceeds via a formal deprotonation of the N-benzyl group followed by trapping of the resulting anion by the alkyne moiety. The key role of the vicinal amide function during the process was pointed out.
UMR 7652 (Ecole Polytechnique/ENSTA/CNRS), Laboratoire Chimie et Procédés, ENSTA-Paristech, 828 Bd des maréchaux, 91120 Palaiseau, France. laurent.elkaim@ensta-paristech.fr.
Laurent
L
El Kaïm
Laurence
L
Grimaud
Simon
S
Wagschal