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Fused s ‐triazino heterocycles. XVIII. 1,3,4,7,11c‐Pentaazabenz[ de ]anthracene and 1,3,4,6,7,11c‐hexaazabenz[ de ]anthracene. Two new ring systems
Author(s) -
Shaw John T.,
Thomas Robert J.,
Herold Sherry A.,
Gfesser Gregory A.,
Isovitsch Ralph A.
Publication year - 1991
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.5570280804
Subject(s) - anthracene , chemistry , yield (engineering) , medicinal chemistry , chloride , ring (chemistry) , triazine , organic chemistry , metallurgy , materials science
The reaction of 2‐amino‐4‐chloro‐6‐methylpyrimidine ( 3a ) with trimethylacetyl chloride gave 4‐chloro‐6‐methyl‐2‐trimethylacetamidopyrimidine ( 5 ). This latter compound with excess anthranilonitrile gave in one step 2‐ t ‐butyl‐5‐methyl‐1,3,4,7,11c‐pentaazabenz[ de ]anthracene ( 6a ). To prepare 2‐ t ‐butyl‐5‐dimethylamino‐1,3,4,6,7,11c‐hexaazabenz[ de ]anthracene ( 6b ) it was found necessary to first react 2‐amino‐4‐chloro‐6‐dimethylamino ‐5 ‐triazine ( 3b ) with anthranilonitrile to yield the intermediate product 2‐amino‐4(2‐cyanoanilino)‐6‐dimethylamino‐ s ‐triazine ( 4 ). Reaction of the latter with trimethylacetyl chloride gave 6b .