co0c00024_si_001.pdf (2.66 MB)
Static Combinatorial Chemistry: A High-Pressure Approach to the Synthesis of Macrocyclic Benzoamide Libraries
journal contribution
posted on 2020-03-20, 13:48 authored by Grzegorz Pikus, Agata Tyszka-Gumkowska, Janusz JurczakWe
investigated the yield and distribution of macrocyclic products formed
in combinatorial libraries (CLs) obtained via double-amidation reactions
of methyl diesters with α,ω-diamines. The application
of the static combinatorial chemistry (SCC) approach allowed us to
generate a large number of macrocyclic diamides and tetraamides in
single experiments. We show that high-pressure conditions accelerate
the macrocyclization process but also have a great impact on the distribution
of macrocyclic products in the presented libraries, promoting the
formation of macrocyclic compounds and eliminating the linear ones.
The distribution of macrocyclic products was also found to be strongly
dependent on the structural features of the substrates employed. Furthermore,
in three- and four-substrate CLs we observed the formation of a new
type of hybrid tetraamides consisting of three different components.