Acetic anhydride mediated condensation of aromatic o-diacid dichlorides with benzimidazoles to provide electro-reducible p-dione adducts

详细信息	查看全文 | 推荐本文 |

• 作者：Eamonn Joyce ; Paul Kavanagh ; Dó ; nal Leech ; Jolanta Karpinska ; Patrick McArdle ; Fawaz Aldabbagh ; ^{fawaz.aldabbagh@nuigalway.ie}
• 关键词：Synthetic methods ; Nitrogen heterocycles ; Cyclic voltammetry ; Stacking interactions
• 刊名：Tetrahedron Letters
• 出版年：2012
• 期刊代码：109_00404039
• 类别：ch
• 出版时间：18 July, 2012
• 卷：53
• 期：29
• 页码：3788-3791
• 文件大小：3049 K

摘要

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 that p-dione is capable of two consecutive one-electron-reductions with formal potentials influenced by the fused (hetero)aromatic and substituent effects.