Synthesis of 1-{6-(2-methylbenzoyl)-N-ethylcarbazole-3-yl}-ethane-1-one oxime O-acetate

Abstract

1-{6-(2-Methylbenzoyl)-N-ethylcarbazole-3-yl}-ethane-1-one oxime O-acetate, an excellent two-photon carbazole photoinitiator, was synthesized with moderate yield (76.9%) starting from the successive o-methyl benzoylation and acetylation of N-ethylcarbazole, followed by oximation and esterification in the article. The structure was confirmed by 1 H-NMR, 13 C-NMR, and IR. The by-product acetic acid in the neutralization of hydroxylamine hydrochloride is effectively utilized in esterification with the aid of the one-pot process. In particular, the phase transfer technique is applied to overcome the deficiency of low reaction rate caused by heterogeneous reaction conditions in esterification.

Synthesis and Structure-Activity Relationship of <i>N</i>-Substituted Carbazole Oxime Ester Photoinitiators

“…All the reagents were of analytical grade and used as received without further purification. OXE-02 was synthesized in the laboratory [21].…”