“…In this respect, many of these derivatives have been used as multiple fluorescent chemosensors, in an electron transport layer of an organic light emitting device, as biomarkers of hypoxic tumor cells, and as a receptor in fluorescent high-affinity ligand in dopamine D3. [11][12][13][14] In connection with the increasing interest of adoption of new synthetic methods in drug discovery, and in continuation to our recent applications of carbon-Michael [15][16][17][18] as well as aza-Michael 16 addition reactions as powerful tools for the synthesis of nitrogen containing heterocycles and their corresponding bisheterocycles, 15,17,[19][20][21][22][23][24][25][26] we report herein our investigation on the reactivity of 2-(3H-imidazo [4,5-b]pyrid-2yl)acetonitrile towards arylidenemalononitriles and bis-arylidenemalononitriles aiming at synthesizing novel mono-and bis-imidazo[1,2-a:5,4-b']dipyridine-6,8-dicarbonitriles. In addition, a theoretical density functional theory (DFT) study aims to determine the more stable regioisomer of the two possible expected isomeric products from the mentioned reactions as well as to investigate the efficacy of the target compounds as suitable candidate for NLO material.…”