Switching between ring closed and open N-incorporated heterocycles with tuneable charges and modular reactivity based upon 5-(2-bromoethyl)phenanthridinium bromide

Abstract

5-(2-bromoethyl)phenanthridinium bromide (BEP) undergoes a 3-step-one-pot cyclisation reaction with primary amines allowing the facile synthesis of a vast library of heterocycles. A diverse range of primary aryl amines were explored as reactants to gain insight into the product isolated as a result of the steric and electronic effects of the aryl precursors. Analysis and reaction monitoring with UV-vis and NMR spectroscopy revealed that excessively electron withdrawing groups and sterically hindered amines do not allow for isolation of the common neutral tetrahydroimidazophenanthridine (TIP) structure but allow either the isolation of the charged dihydroimadazophenanthridinium (DIP) or aminoethylphenanthridinium (AEP) products.

Synthesis and Alkyne Insertion Reactions of NHC-Based Cyclometalated Ruthenium(II) Complexes

“…In addition, imidazophenanthridinium (IPs) and dihydroimidazophenanthridinium derivatives (DIPs) (Chart ) have recently garnered much attention due to their biological activity and other properties. , However, only a few synthetic routes have been reported, and most of these routes are not very efficient . Here, a simple and efficient procedure leading to these kinds of imidazolium salts has been developed.…”

A Mild and Efficient Method to Functionalize Azines (Quinoline, Isoquinoline, and Phenanthridine) Using Acetylenic Esters and Heterocyclic NH or 1,3‐Dicarbonyl Compounds

“…They are shown important biological activities, including antitumor, anticancer, antibacterial, and antipyresis . Molecules containing the phenanthridinium core are an important subset of heteroaromatic cations as they have numerous applications as drugs, DNA targeting agents, dyes, and DNA probes . As previously reported , the reaction between phenanthridine and dimethyl acetylenedicarboxylate (2 mol equiv) led to the formation of a new ring on the phenanthridine core.…”