Premium
Fused‐ s ‐triazino heterocycles. XI. Displacement reactions of 7,9‐dichloro‐2,5‐bis(trichloromethyl)‐1,3,4,6,9b‐pentaazaphenalene
Author(s) -
Shaw John T.,
Rapple Rodney S.,
Hicks John C.,
Vossers John T.
Publication year - 1984
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.5570210232
Subject(s) - chemistry , chlorine , chlorine atom , nucleophile , medicinal chemistry , substitution reaction , displacement (psychology) , nucleophilic substitution , organic chemistry , catalysis , psychology , psychotherapist
The preparation of 7,9‐dichloro‐2,5‐bis(trichloromethyl)‐1,3,4,6,9b‐pentaazaphenalene ( 1e ) by the chlorination of 2‐trichloromethyl‐5‐methyl‐1,3,4,6,9b‐pentaazaphenalene ( 1a ) using molecular chlorine is described. Displacement of one or both trichloromethyl groups of 1e by a variety of nucleophiles led to the corresponding 7,9‐dichloro‐2,5‐bis‐substituted or 7,9‐dichloro mixed 2,5‐disubstituted derivatives. The reaction of 1a with N ‐chlorosuccinimide proved not to be a useful route to 1e but instead led primarily to substitution of positions 7 and/or 9 by chlorine.