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Abstract
A preparative scalable approach to 3,7-bifunctional 5H-pyrrolo[3,2-c]pyridazines and 3,5-bifunctional 7H-pyrrolo[2,3-c]pyridazines with a diverse set of functionalities (C(sp2)-Br/I, CO2H, CHO, SO2Cl, NH2) in the pyrrole and active chlorine atom in the pyridazine parts, respectively, was developed. Due to the suitability of these groups for synthesizing various derivatives of the above-mentioned rings, they can be utilized for both lead optimization and functional material design. Carbonylation route catalyzed by Pd produced the corresponding esters of 7H-pyrrolo[2,3-c]pyridazine-3-carboxylic acid or 5H-pyrrolo[3,2-c]pyridazine-3-carboxylic acid, which were involved in the reduction reactions as well. A solution for the selective preparative partial hydrogenation of the pyrrole ring to dihydropyrrole was also proposed. As a result, a convenient tool for implementing the "nitrogen walk" approach around indole and azaindole scaffolds was suggested for medicinal chemistry purposes.
