A Facile Synthesis ofN-H- andN-Substituted Acridine-1,8-diones under Sonic Condition

S Sudha,M A Pasha

doi:10.1155/2013/930787

Abstract

Synthesis of an assembly of structurally important N-H- and N-substituted acridine-1,8-diones by CAN (ceric ammonium nitrate) catalysed one-pot four-component reaction of electron-deficient and electron-rich aromatic aldehydes and aromatic amines or ammonium acetate and dimedone or cyclohexyl-1,3-diones at 26°C under sonic condition is reported. The method is clean and energy efficient as it uses a greener method and an eco-friendly catalyst.

Highlights

Acridine and its derivatives are important structural motifs possessing antimalarial, antiviral, and antiallergic properties [1,2,3]; acridines act as potent drugs for antitumor activity both in vitro and in vivo against a range of murine and human tumors [4]
There are a few reports in the literature on the three-component Hantzschtype condensation of aromatic aldehydes, anilines, and dimedone via traditional heating in organic solvents [10, 11], under microwave irradiation [12], and in ionic liquids [13]
To the best of our knowledge, the synthesis of acridines from fluorinated aromatic amines and heterocyclic amines using an inexpensive catalyst under sonic condition is not reported yet

Summary

Introduction

Acridine and its derivatives are important structural motifs possessing antimalarial, antiviral, and antiallergic properties [1,2,3]; acridines act as potent drugs for antitumor activity both in vitro and in vivo against a range of murine and human tumors [4]. They are found to act as fluorescent molecular probes for monitoring polymerization processes [5] and are used as n-type semiconductors and in the electroluminescent devices. To the best of our knowledge, the synthesis of acridines from fluorinated aromatic amines and heterocyclic amines using an inexpensive catalyst under sonic condition is not reported yet. The use of an inexpensive and versatile catalyst, CAN, in conjunction with ultrasound is considered to be economical and beneficiary in organic synthesis [20]

Methods

Spectral Data

Results and Discussion

Conclusions