A facile synthesis of 2,7-diazapyrene

✍ Scribed by Chariklia Sotiriou-Leventis; Zhan Mao

• Publisher: Journal of Heterocyclic Chemistry
• Year: 2000
• Tongue: English
• Weight: 218 KB
• Volume: 37
• Category: Article
• ISSN: 0022-152X
• DOI: 10.1002/jhet.5570370645

✦ Synopsis

Abstract

2,7‐Diazapyrene is synthesized in three high‐yield steps from commercially available 1,4,5,8‐naphthalene tetracarboxylic dianhydride, which first reacts with concentrated ammonium hydroxide solution at room temperature to give 1,4,5,8‐naphthalenetetracarboxylic diimide (96%). The latter compound is subsequently reduced with borane in refluxing tetrahydrofuran to give 1,2,3,6,7,8‐hexahydro‐2,7‐diazapyrene (77%), which in turn is oxidized with manganese dioxide in refluxing benzene giving 2,7‐diazapyrene (71%).