This study focuses on the development of new synthetic pathways to monosubstituted
biguanides from amines. An exhaustive comparison of the conditions and reagents used
for biamidine transfer was performed. New reagents were synthesized and optimized
conditions for the synthesis of substituted biguanides under mild conditions were
developed. Eventually, two high-yielding and straightforward protocols for the transfer
of a biamidine group to various amines are proposed and their scope and limitations
have been explored. These conditions include: i) a direct chromatography-free procedure
and ii) an eco-friendly procedure in water compatible with bioinspired molecules.
They are particularly efficient for the demanding conversion of aliphatic amines.
Key words
biguanide - biamidine transfer - mild conditions - biocompatible protocol - guanidine
derivatives
