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Pyrrolo[1,2-a]quinoxalines: novel synthesis via annulation of 2-alkylquinoxalines. 2012

Sven Ammermann, and Christian Hrib, and Peter G Jones, and Wolf-Walther du Mont, and Wolfgang Kowalsky, and Hans-Hermann Johannes
Labor für Elektrooptik am Institut für Hochfrequenztechnik, Technische Universität Braunschweig, Postfach 3329, 38023 Braunschweig, Germany.

In an attempt to synthesize a novel homoleptic complex 3 from 2-methyl-3-phenylquinoxaline 1 and Ir(acac)(3) for application as a triplet emitter in OLEDs (organic light-emitting diodes) no cyclometalation was observed. Instead, an annulation to 1-methyl-4-phenylpyrrolo[1,2-a]quinoxaline 2 was observed. Since pyrroloquinoxalines are potentially bioactive and few paths for their synthesis are known, selected reactions and conditions were investigated, suggesting Ir(acac)(3) as catalyst and proving glycerol to be a reactant.

UI MeSH Term Description Entries
D008958 Models, Molecular Models used experimentally or theoretically to study molecular shape, electronic properties, or interactions; includes analogous molecules, computer-generated graphics, and mechanical structures. Molecular Models,Model, Molecular,Molecular Model
D011758 Pyrroles Azoles of one NITROGEN and two double bonds that have aromatic chemical properties. Pyrrole
D011810 Quinoxalines Quinoxaline
D005990 Glycerol A trihydroxy sugar alcohol that is an intermediate in carbohydrate and lipid metabolism. It is used as a solvent, emollient, pharmaceutical agent, or sweetening agent. 1,2,3-Propanetriol,Glycerin,1,2,3-Trihydroxypropane,Glycerine
D000478 Alkylation The covalent bonding of an alkyl group to an organic compound. It can occur by a simple addition reaction or by substitution of another functional group. Alkylations
D015394 Molecular Structure The location of the atoms, groups or ions relative to one another in a molecule, as well as the number, type and location of covalent bonds. Structure, Molecular,Molecular Structures,Structures, Molecular

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