Several thieno[2,3-h]-/[3,2-h]- and [2,3-f]quinolines have been synthesised from 2,3-dihalogenated pyridines or -quinolines by site-selective Pd catalysed cross-coupling reactions and Brønsted acid mediated cycloisomerisations as the final key step.

Diarylated 2-(trifluoromethyl)quinolines, containing two identical aryl groups, were prepared by Suzuki-Miyaura crosscoupling reaction of 4,6-dibromo-2-(trifluoromethyl)quinoline. In order to obtain quinolines, containing two different aryl groups, the starting material had to be modified in order to obtain a high degree of regioselectivity of the reaction. The 6bromo-4-chloro-2-(trifluoromethyl)quinoline with arylboronic acids allowed for a one-pot, two-step synthesis of various products in very good yields. The synthesized derivatives were evaluated for their potential to inhibit ecto-5'-nucleotidase, both human and rat source. Most derivatives exhibited selective inhibition on human ecto-5'-nucleotidases (h-e5'NT) with significant inhibitory concentration (IC 50 ) values. The results were evaluated by docking studies.[a] Dr.

4‐Bromo‐2,3,5‐trichloro‐6‐iodopyridine has been synthesized for the first time and applied in chemo‐ and site‐selective Suzuki–Miyaura cross‐coupling reactions. This novel starting material allows the selective synthesis of pentaarylpyridines with up to four different aryl substituents.