A Facile Synthesis of 2,7-diazapyrene
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%).
L. Sotiriou-Leventis and Z. Mao, "A Facile Synthesis of 2,7-diazapyrene," Journal of Heterocyclic Chemistry, John Wiley & Sons, Jan 2000.
The definitive version is available at http://dx.doi.org/10.1002/jhet.5570370645
American Chemical Society
Petroleum Research Fund
University of Missouri Research Board
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