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Synthesis of 2,7‐disubstituted‐4,5,9,10‐tetraazapyrenes
Author(s) -
Castle Raymond N.,
Guither William D.,
Hilbert Peter,
Kempter Fritz E.,
Patel Natu R.
Publication year - 1969
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.5570060413
Subject(s) - chemistry , raney nickel , hydrogen peroxide , catalysis , alkali metal , catalytic hydrogenation , nickel , medicinal chemistry , oxide , nuclear chemistry , organic chemistry
2,7‐Dimethyl‐4,5,9,10‐tetraazapyrene (VI) was synthesized by the catalytic hydrogenation of 4,4′‐dimethyl‐2,2′,6,6′‐tetranitrobiphenyl (IIa) with W‐2 Raney nickel in the presence of alkali. 4,4′‐Dicarbomethoxy‐2,2′,6,6′‐tetranitrobiphenyl (IIc) under similar conditions in neutral medium gave 4,4′‐dicarbomethoxy‐2,2′,6,6′‐tetraaminobiphenyl (IV) which on oxidation gave 2,7‐dicarbomethoxy‐4,5,9,10‐tetraazapyrene (V). 2,7‐Dimethyl‐, 2,7‐dimethoxy‐, and 2,7‐diacetamido‐4,5,9,10‐tetraazapyrene di‐ N ‐oxides (III a,b,c) were obtained by catalytic reduction of the corresponding 4,4′‐disubstituted‐2,2′,6,6′‐tetranitrobiphenyls with W‐7 Raney nickel in the presence of alkali. Compound VI on oxidation with hydrogen peroxide gave the di‐ N ‐oxide (IIIa).