Premium
Acridine Variations for Coordination Chemistry
Author(s) -
Omolo Kevin O.,
Bacsa John,
Sadighi Joseph P.
Publication year - 2020
Publication title -
israel journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.908
H-Index - 54
eISSN - 1869-5868
pISSN - 0021-2148
DOI - 10.1002/ijch.202000006
Subject(s) - chemistry , acridine , moiety , nucleophilic aromatic substitution , acridone , methoxide , bromine , nucleophile , lithium (medication) , combinatorial chemistry , nucleophilic substitution , medicinal chemistry , ion , stereochemistry , organic chemistry , catalysis , medicine , endocrinology
This study describes the synthesis of an acridone through the directed lithiation of a diarylamine, and elaboration via the 4,5‐dibromoacridone. The bromo substituents are amenable to Suzuki‐Miyaura coupling. Conversion to a 9‐chloro‐4,5‐dibromoacridine, followed by bromine‐lithium exchange, allows the preparation of a 4,5‐bis (phosphino)‐9‐chloroacridine. The 9‐chloro moiety undergoes nucleophilic aromatic substitution by methoxide or an aryloxide. One‐electron reduction of a 9‐(aryloxy)‐4,5‐bis(phosphino)acridine affords a stable radical anion.