Regioselective Bromination of a Thymine-Acridine Conjugate by N-Bromosuccinimide
Document Type
Article
Publication Title
Synthetic Communications
Department
Chemistry
ISSN
0039-7911
Volume
40
Issue
8
DOI
10.1080/00397910903061050
First Page
1192
Last Page
1201
Publication Date
1-1-2010
Abstract
A thymine and acridine conjugate (1), containing a benzylic carbon of thymine and an electron-rich aromatic ring (acridine) within the same molecule, was synthesized. Treatment of 1 with N-bromosuccinimide (NBS) in anhydrous chloroform in the presence of azobisisobutylnitrile produced a dibromo-substituted thymine-acridine conjugate (7) as a major product, in which the bromination was only observed on the acridine ring. Nuclear Overhauser effect (NOE) difference spectroscopy revealed that the actual bromination substitution was on C-2 and C-7 of acridine. Our results suggest that electrophilic aromatic substitution, not the expected benzylic radical reaction, takes place predominantly even when 1 is subjected to the NBS reaction condition, which favors radical processes. In addition, such selectivity is clearly solvent dependent.
Recommended Citation
Liu, W.,
Navarro, E.,
Franz, A. H.,
&
Xue, L.
(2010).
Regioselective Bromination of a Thymine-Acridine Conjugate by N-Bromosuccinimide.
Synthetic Communications, 40(8), 1192–1201.
DOI: 10.1080/00397910903061050
https://scholarlycommons.pacific.edu/cop-facarticles/144
