
Journal of the Chemical Society. Perkin transactions I p. 988 - 990 (1981)
Update date:2022-09-26
Topics:
Abou-Teim, Omar
Hacker, Nigel P.
Jansen, Robert B.
McOmie, John F. W.
Perry, David H.
Condensation of the 4-hydroxy- (3), 4,5-dichloro- (4), 3,6-dimethoxy- (5), and 4,5-benzo- (9) derivatives of benzocyclobutene-1,2-dione with o-phenylenediamine gave the corresponding 5,10-diazabenzobiphenylenes, (13)-(16) whereas the similar condensation of the 4-methoxy- (6), 4,5-dimethoxy- (7), and 4,5-dibromo- (8) derivatives, also cyclobuta(l)phenanthrene-1,2-dione, unexpectedly gave derivatives of dibenzo<1,4>diazocine-6,11(5H,12H)-dione (20)-(23).Treatment of the 4-hydroxy-dione (3) with 1.4 equivalents of o-phenylenediamine gave 1,2-bis-(2-aminophenylimino)benzocyclobuten-4-ol (18) and condensation of the phenanthrodione with the diamine in presence of phosphoric anhydride gave dibenzisoindolo<2,1-a>benzimidazol-15-one (25).
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Doi:10.1021/jo049025x
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