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Eamonn Joyce, Paul Kavanagh, Dónal Leech, Jolanta Karpinska, Patrick McArdle, Fawaz Aldabbagh
Tetrahedron Letters
Acetic anhydride mediated condensation of aromatic o-diacid dichlorides with benzimidazoles to provide electro-reducible p-dione adducts
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Synthetic methods Nitrogen heterocycles Cyclic voltammetry Stacking interactions ANTITUMOR AGENTS REDUCTIVE ACTIVATION QUINONES DESIGN PART
Acetic anhydride mediates a facile and rapid condensation of benzimidazole with aromatic o-diacid dichlorides to precipitate p-dione adducts in excellent yields. Condensation with pyridine-3,4-dicarbonyl dichloride produced a 1:1 mixture of isomeric p-diones. The X-ray crystal structure of one of the latter isomers revealed unusual high density, and inter-layer separation similar to graphite. Cyclic voltammetry demonstrated the p-dione is capable of two consecutive one-electron-reductions with formal potentials influenced by the fused (hetero)aromatic and substituent effects. (C) 2012 Elsevier Ltd. All rights reserved.
DOI 10.1016/j.tetlet.2012.05.047
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