Ultrasound-Assisted Synthesis of Fluorescent Azatetracyclic Derivatives: An Energy-Efficient Approach.

Abstract

We report here an energy-efficient and straight synthesis of two new classes of derivatized fluorescent azatetracycles under ultrasound (US) irradiation. A first class of azatetracyclic compounds was synthesized by heterogeneous catalytic bromination of the α-keto substituent attached to the pyrrole moiety of the tetracyclic cycloadducts, while for the second, one class was synthesized by nucleophilic substitution of the bromide with the azide group. Comparative with conventional thermal heating (TH) under US irradiation, both types of reactions occur with substantially higher yields, shortened reaction time (from days to hours), lesser energy consumed, easier workup of the reaction, and smaller amounts of solvent required (at least three to five-fold less compared to TH), which make these reactions to be considered as energy efficient. The derivatized azatetracycle are blue emitters with λmax of fluorescence around 430–445 nm. A certain influence of the azatetracycle substituents concerning absorption and fluorescent properties was observed. Compounds anchored with a bulky azide group have shown decreased fluorescence intensity compared with corresponding bromides.