Derivatization of N-propargyl-3-nitropyrrole by sonogashira carbon-carbon coupling

Pyrrole (1) is included in the class of heterocyclic compounds because it contains nitrogen atoms as well as carbon and hydrogen atoms in its structure. It is included in the group of aromatic compounds because it is planar and complies with the Hückel (4n+2) π electron rule. Pyrrole is a five-membered compound isolated from coal tar for the first time. The pyrrole skeletal system is frequently encountered in heterocyclic studies. It is possible to see this skeletal system in many pharmaceutical products and the structure of natural compounds. The thesis includes information about some of these compounds. In this thesis study, the pyrrole skeleton was modified by various chemical methods, and it became possible to synthesize different compounds. In the first step of the research, the pyrrole molecule was mono-nitrosated at positions 2 and 3. The study continued with the 3-nitropyrrole compound, and a propargyl group was attached to the nitrogen atom of pyrrole. Thus, the key structure of the study, N-propargyl-3-nitropyrrole (21) compound, was isolated. Then, the derivatization process was carried out by attaching various aromatic groups to the terminal alkyne end of the propargyl group in structure 21 by the Sonogashira carbon-carbon (C-C) coupling reaction. The structures of the compound synthesized during the research were explained through characterization processes (melting points, IR, NMR, and HRMS analyses).