Metal ion activation of nitriles. Syntheses of 1,3-bis(arylimino)isoindolines

Investigations into the Coordination Chemistry of 1,3-Bis(2’-benzimidazolyl­imino)isoindoline

“…[22] For the purposes of this report, we'll be focusing on its properties to form a metal chelate similar to bis(iminopyridyl)-isoindoline. [23,24] Specifically, herein we will present work on the metal binding of 1,3-bis(2'-benzimidazolylimino) isoindoline (1, Scheme 1) with elements from the first row of the transition metals.…”

“…The single exceptions are a manganese adduct and a N-methylated variant of 1 with copper. [24,26] In this report, we present the first structural elucidation of 1, as well as a series of first row transition metal adducts of 1. All of the structures presented here exhibit hydrogen bonding, and in some cases extensive hydrogen bonding resulting in large hydrogen-bonded networks in the solid state.…”

1,3-Bis(5′-methyl-4′-phenyl-2′-thiazolylimino)isoindoline

“…Fusing phthalonitrile with primary amines requires high temperature (180-190˝C) but there are advantages like shorter reaction time and solvent-free conditions (Scheme 1). The addition of a primary amine to phthalonitrile results in an intramolecular cyclization to form a relatively stable 1-arylimino-3-iminoisoindoline, which may undergo addition of a second amine with loss of ammonia and formation of the BAI via nucleophilic addition reaction [8]. The preparation of the title compound (1) has been carried out accordingly, yielding 80% orange product.…”

Synthesis, structure and DNA interaction of cobalt(III) bis-complexes of 1,3-bis(2-pyridylimino)isoindoline and 1,4,7-triazacyclononane

“…The ligand was prepared according to the literature procedure [40]. In a round-bottom flask, phthalonitrile (1.28 g, 10 mmol), 2-aminopyridine (1.97 g, 21 mmol) and calcium chloride (0.1 g, 1 mmol) in 1-butanol (20 mL) were heated at reflux for 48 h. On cooling the solution, a crystalline solid (HL) was isolated.…”