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Synthesis of 5,12‐diazadibenz[ a,h ]anthracene
Author(s) -
Klemm L. H.,
Johnson W. O.,
Weisert Annekäte
Publication year - 1971
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.5570080516
Subject(s) - chemistry , anthracene , formylation , yield (engineering) , condensation , benzene , medicinal chemistry , terphenyl , phenanthridine , organic chemistry , hydride , isomerization , hydrogen , catalysis , materials science , physics , metallurgy , thermodynamics
5, 12‐Diazadibenz[ a,h ]anthracene ( 20 ) was synthesized in 21% overall yield for seven steps. Salient features of the synthesis include the initial, one‐step conversion of trans, trans ‐1,4‐bis‐(β‐nitrovinyl)benzene into 2,2″‐dinitro‐ p ‐terphenyl by Diels‐Alder condensation plus elimination, monocyclization of the derived 2,2″‐diformylamino‐ p ‐terphenyl to give 8‐(2‐amino‐1‐phenyl)‐phenanthridine ( 10 ) in the presence of fortified polyphosphoric acid, and accomplishment of a second cyclization step only after reduction of the heteroring in 10 (by means of diisobutyl‐aluminum hydride) plus formylation. The 6‐methyl and 6,13‐dimethyl derivatives of 20 were prepared similarly.