Recent Advances in the Synthesis of Acridines and Phenazines

Abstract

Acridines and phenazines are common motifs in bioactive compounds and natural products. Many excellent works on the synthesis of these skeletons starting from diaryliodonium salts, benzaldehydes, anthranils, azobenzenes, and nitrosobenzenes have been reported. In this overview, we highlight several recent elegant works on the synthesis of acridines and phenazines.1 Introduction2 Synthesis of Acridines3 Synthesis of Phenazines4 Conclusion

Synthetic strategies of phenazine derivatives: A review

“…The same year, Gajula and co-workers [83] reported an efficient approach of using condensation method in one pot to synthesize of various substituted phenazine derivatives (43)(44)(45)(46)(47)(48)(49)(50). As shown in Scheme 8, in general, 2-naphtol occurred self-coupling to form the intermediate of 1, 2-naphthoquinones had condensation in one pot to obtain target compound in good to excellent yields.…”

“…In sharp contrast, these synthetic strategies epitomize powerful alternatives with sustainable, facile, and highefficient principles for the formation of complex molecules, such as electrochemical strategy, biosynthesis, microwave method, supramolecular catalysis, photocatalysis, and some chemical synthesis [16,[44][45][46][47][48][49][50][51][52][53][54][55][56]. Notably, these strategies effectively avoid the major drawbacks of traditional methods and simultaneously provide concise process to furnish structurally various phenazine derivatives in good to excellent yields [49,[57][58][59][60][61][62][63].…”

Monowave microwave activation: green formation of carbon-carbon bond in solvent free Tiedtke reaction

“…In addition, several therapeutic agents are based on amino-9-acridine moiety derivating [13][14][15] from acridones, such as tacrine, ethacridine (abortifacient), nitracrine (antineoplastic), mepacrine (antimalarial properties), amsacrine… Considering the great interest of the reaction of Tiedtke, we decided to resume this reaction under microwave activation by using an adequate reactor (Monowave 300, Anton Paar). 16 The monomode conditions and the controlled emission of microwaves allow reproducible and scaled up experiments.…”

“…Some were generally described in the old literature but were poorly documented. We took opportunity of their syntheses to describe and properly attributed the 1 H and 13 C NMR spectra of the tetrahydroacridones thanks to HSQC, HMBC, COSY and DEPT experiments.…”

Vinyldiazo Compounds as 3-Carbon Radical Acceptors: Synthesis of 4-Fluoroacridines via Visible-Light-Promoted Cascade Radical Cyclization

“…Consequently, the development of efficient methods for the construction of this compound class has been a significant task in heterocyclic chemistry. Ring closures of suitable precursors to form the pyridine skeleton are the most widely applied methods for the preparation of acridines . Transition-metal-catalyzed benzannulation of quinoline derivatives has also been reported .…”