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A facile synthesis of 2,7‐diazapyrene
Author(s) -
SotiriouLeventis Chariklia,
Mao Zhan
Publication year - 2000
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570370645
Subject(s) - chemistry , naphthalene , ammonium hydroxide , yield (engineering) , tetrahydrofuran , benzene , manganese , borane , hydroxide , diimide , organic chemistry , medicinal chemistry , nuclear chemistry , polymer chemistry , catalysis , perylene , molecule , materials science , solvent , metallurgy
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%).