Synthesis of a Fluorescent Acridone Using a Grignard Addition, Oxidation, and Nucleophilic Aromatic Substitution Reaction Sequence

Abstract

A three-pot synthesis oriented for an undergraduate organic chemistry laboratory was developed to construct a fluorescent acridone molecule. This laboratory experiment utilizes Grignard addition to an aldehyde, alcohol oxidation, and iterative nucleophilic aromatic substitution steps to produce the final product. Each of the intermediates and the acridone product of the synthesis are analyzed by common techniques available in most undergraduate chemistry laboratories, such as melting point, TLC, IR spectroscopy, UV-Vis spectroscopy, and fluorescence spectroscopy. Yields for each transformation in the synthesis are generally moderately low to good (20–90%) and nearly all of the students (>90%) who attempted the synthesis were able to produce the final acridone product.

Self-assembly of reversed bilayer vesicles through pnictogen bonding: water-stable supramolecular nanocontainers for organic solvents

“…To test this, uorescent dyes rhodamine B (RhB) and an acridonebased (Ac) dye were post-synthetic encapsulated and imaged. 51 To capture the uorescent dyes, 0.7 mg of RhB, or 0.1 mg of Ac were added to acetone or chloroform, respectively, containing 0.25 mM of Sb-1 Et . Both samples were sonicated for 5 minutes at 40% probe power amplitude.…”

Discovery-Based SNAr Experiment in Water Using Micellar Catalysis

“…Given the highly varied backgrounds of these students, it was decided to use nucleophilic aromatic substitution (S N Ar) chemistry, a reaction that is particularly relevant to medicinal and pharmaceutical chemistry . A few examples of educational laboratories with this chemistry that also focus on green chemistry have been published, including the use of the surfactant Triton X in the formation of C–S bonds. − The experiment discussed herein features nucleophilic aromatic substitution (S N Ar) reactions and is suitable for a first or second-semester organic chemistry laboratory. This experiment provides an opportunity to introduce students to systems thinking, as they are taught to consider not only how well their reaction achieves the desired product but also other factors that affect or are affected by the way in which the reaction is performed.…”

Nucleophilic Aromatic Substitution—Addition and Identification of an Amine

“…Given the importance and versatility of this reaction, other than Sanger-type reactions, we could find few examples of nucleophilic aromatic substitution in this Journal . − Herein we report this communication as an experiment that exemplifies this versatile reaction as a teaching tool by engaging students in a novel exercise that allows them to determine the identity of an unknown amine reagent.…”