This study is divided into two parts: experimental and theoretical. In the experimental
part, N-propargyl-substituted pyrrolylamide derivatives are synthesized in five steps starting
from pyrrole. The main features of this procedure are (i) the synthesis of 2- and
3-nitropyrrole, (ii) the introduction of a propargyl group on the nitrogen atom of
the pyrrole, (iii) coupling of various substituents with the alkyne functionality
by the Sonogashira reaction, (iv) synthesis of pyrrolylimides by a tin-catalyzed reaction
with phthalic anhydride, and, finally, (v) reduction of pyrrolylimides with sodium
borohydride (NaBH4) in the presence of water. The theoretical part concerns the reduction mechanism
of the pyrrolylimide by NaBH4. The hybrid functional B3LYP in density functional theory is used to determine and
discuss the energetics of the compounds.
Key words
heterocycles - alkynes - coupling - molecular modeling - reduction
