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Fused s ‐triazino heterocycles. X. Displacement reactions of 7,9‐dibromo‐2‐tribromomethyl‐5‐trichloromethyl‐1,3,4,6,9b‐pentaazaphenalene and 7,9‐dibromo‐2,5‐bis(tribromomethyl)‐ 1,3,4,6,9b‐pentaazaphenalene
Author(s) -
Shaw John T.,
Starkey Kenneth D.,
Pelliccione David J.,
Barnhart Sharon L.
Publication year - 1983
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.5570200450
Subject(s) - chemistry , nucleophile , pyrrolidine , displacement (psychology) , medicinal chemistry , group (periodic table) , organic chemistry , catalysis , psychology , psychotherapist
The preparation of 7, 9‐dibromo‐2‐tribromomethyl‐5‐trichloromethyl‐1, 3, 4, 6, 9b‐pentaazaphenalene ( 1c ) and 7, 9‐dibromo‐2, 5‐bis(tribromomethyl)‐1, 3, 4, 6, 9b‐pentaazaphenalene ( 1d ) is described. Reaction of 1c with various nucleophiles converted it to the corresponding 7, 9‐dibromo‐2, 5‐bis‐substituted derivatives, the tri‐halomethyl groups serving as leaving groups. Displacement, first of one tribromomethyl group on 1d by pyrrolidine, and then by various nucleophiles on the remaining tribromomethyl group led to several mixed 2, 5‐disubstituted derivatives.