Synthesis of Fused Azo-linked Acridine Derivatives Using MCM-41/Ag2S-RHA Nanocomposite

Abstract

Introduction: In this study, the synthesis of azo-linked acridine by the reaction of dimedone and synthesized diazoaryl-(2-amino-5-(phenyl)methanone using Ag2S/RHA-MCM-41nanocomposite is reported.

Materials and methods: The synthesized catalyst was characterized by FT-IR, XRD, and SEM. According to the obtained results, Ag₂S/RHA-MCM-41 nanocomposite exhibited high activity in the synthesis of azo-acridine derivatives based on desirable yields and reaction time. Products were prepared in 1.5-2 h and with 88-93% yield. In all the reactions, the catalyst could be easily removed and reused, and its catalytic activity was maintained after five uses and did not decrease significantly. The structures of all newly synthesized products were characterized by spectroscopic spectra (FT-IR, ¹H NMR, ¹³C NMR) and elemental analyses.

Results and discussion: The results of the study showed that ionic liquid [DBU]OAc (entry 8) and MCM- 41/Ag2S-RHA nanocomposite (entry 8) possessed better efficiency and shorter time than other reaction conditions.

Conclusion: In this study, new azo-linked acridine derivatives were synthesized by the reaction of different azo derivatives and dimedone using MCM-41/Ag2S-RHA nanocomposite, and the reaction products were obtained in 1.5-2 h with an efficiency of 88-93%. The short reaction time and high efficiency of the obtained products indicated the high efficiency of this method. In all the reactions, MCM-41/Ag2S-RHA nanocomposite could be easily removed and reused. Its catalytic activity was maintained in the sample reaction after five runs and did not decrease significantly.

Keywords: Acridine; MCM-41/Ag2S-RHA; azo-synthesis; dimedone; nanocomposite; spectroscopic..