9‐Azidoacridine and 9‐acridinylnitrene

Abstract

Matrix photolysis as well as flash vacuum thermolysis (FVT) of 9‐azidoacridine affords 9‐acridinylnitrene, which is characterized by its IR and ESR spectra and is photochemically inert. FVT above 600 °C yields a mixture of the five isomeric cyanocarbazoles. Microwave‐assisted reaction with diethyl‐ and dipropylamines in solution affords acridinylformamidine and acridinylpropionamidine, respectively. Microwave‐assisted reaction with dimethylamine causes nucleophilic displacement of the azido group. Microwave‐assisted 1,3‐dipolar cycloaddition with phenylacetylene yields the two regioisomeric 9‐(4‐ and 5‐phenyl‐1,2,3‐triazol‐1‐yl)acridines, whose structures were established by X‐ray crystallography. Copyright © 2010 John Wiley & Sons, Ltd.

Synthesis, computational study and biological evaluation of 9-acridinyl and 1-coumarinyl-1,2,3-triazole-4-yl derivatives as topoisomerase II inhibitors

“…9-Azidoacridine ( 1 ) was prepared by nucleophilic substitution of 9-chloroacridine in the presence of sodium azide under dry conditions 29 , and 3-azido-2 H -chromen-2-one 2 was prepared through cyclisation, hydrolysis, and diazotisation of 2-hydroxylbenzaldehyde as previously described 32 . The propargyl derivatives ( 3 – 7 ) were prepared by conventional alkylation through the reaction of the active nucleophilic centres with propargyl bromide substrate 32 , 33 .…”

Light induced reactions in cryogenic matrices

“…Using a similar strategy, the same research group investigated the matrix photolysis of 9-azidoacridine, 56 which afford the matrix photostable 9-acridinylnitrene.…”

A rapid, chromatography-free route to substituted acridine–isoalloxazine conjugates under microwave irradiation

“…19 The formed crude N-aryl anthranillic acids 3 were then ring closed with POCl3 under microwave irradiation. 20 The desired 9-chloroacridines 4 could be isolated by a variety of methods, vacuum sublimation, vacuum filtration through a pad of silica gel or recrystallisation to give single compounds. Several greener methods have been reported in the literature for the synthesis of N-aryl anthranillic acids including solvent free conditions with microwave irradiation 21 and use of ultrasound in aqueous solution.…”