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Some novel halogenated phenazine derivatives
Author(s) -
Twomey Dermot
Publication year - 1986
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.5570230262
Subject(s) - chemistry , phenazine , halogenation , bromine , aryl , moiety , halogen , medicinal chemistry , amine gas treating , substituent , residue (chemistry) , organic chemistry , alkyl
3‐Amino‐10‐aryl‐2‐arylimino‐2,10‐dihydrophenazines 1 undergo iodination in the 4‐position of the phenazine nucleus yielding compounds which are identical with those obtained by oxidation of appropriate N ‐aryl‐ o ‐phenylenediamines with sodium iodate in the presence of acid. Bromination also takes place in this position but a second bromine atom enters the para ‐position of the arylimino moiety. The isomeric 10‐aryl‐3‐aryl‐amino‐2,10‐dihydro‐2‐iminophenazines 2 yield unstable iodo‐derivatives but undergo bromination in the 1‐and 4‐position of the phenazine nucléus and in the ortho ‐ and para ‐positions of the arylamino substituent. Preliminary chlorination experiments indicate that the substitution pattern is analogous to that established for the brominated products. The removal of bromine and iodine from the phenazine ring by reaction with a primary or secondary amine and their replacement by hydrogen rather than by the amine residue is also recorded.