673. The bromination and nitration of acridine 10-oxide

Acheson, R. M.; Adcock, B.; Glover, George M.; Sutton, L. E.

doi:10.1039/jr9600003367

Cited by 21 publications

(5 citation statements)

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“…The N-oxides were synthesized and purified by the procedures in [25,27,[30][31][32][33][34]. Pyridine, 4-methylpyridine, and quinoline were kept over KOH and distilled.…”

Section: Methodsmentioning

confidence: 99%

Extra Coordination of Zn-Tetraphenylporphine with Pyridine, Quinoline, and Acridine N-Oxides

et al. 2005

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The log K values of zinc tetraphenylporphine (Zn3TPhP) complexes with pyridine, quinoline, and acridine N-oxides and with their nonoxidized analogs, as well as the positions of absorption maxima of the complexes with respect to Zn3TPhP linearly depend on the pK BH + of the ligands in water (methanol, acetonitrile, nitromethane, and acetone) and on Hammett s constants in the absence of steric effects.

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“…The N-oxides were synthesized and purified by the procedures in [25,27,[30][31][32][33][34]. Pyridine, 4-methylpyridine, and quinoline were kept over KOH and distilled.…”

Section: Methodsmentioning

confidence: 99%

Extra Coordination of Zn-Tetraphenylporphine with Pyridine, Quinoline, and Acridine N-Oxides

et al. 2005

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“…60 Direct bromination of 9-acridone in mild conditions (Br 2 , acetic acid) gives the 2,7dibromoacridone 61 but harsher conditions (Br 2 /PBr 3 mixture at 140 °C) yields the desired 9-bromoacridine. 62 To avoid multibromination and/or degradation of the complex, we modified the conditions of Acheson 61,62 by reacting [Ru(bpy) 2 (oxo-dpqp)](PF 6 ) 2 with phosphorus tribromide (PBr 3 ) in DMF at 0 °C for one hour to afford [Ru(bpy) 2 (Br-dpqp)] (PF 6 ) 2 in 78% yield (see Scheme 2). As for chlorination, bromination was confirmed by 1 H NMR with the disappearance of the NH signal and by HRMS with mass peak at m/z 459.5480 (ESI-MS, [M] 2+ ).…”

Section: Functionalization Of the Dipyrido-quinolino-phenazine Ligand...mentioning

confidence: 99%

Synthesis of three series of ruthenium tris-diimine complexes containing acridine-based π-extended ligands using an efficient “chemistry on the complex” approach

et al. 2016

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The preparation and characterization of three series of novel ruthenium(ii) complexes are reported, each series differing by the nature of the ancillary ligands (2,2'-bipyridine - bpy, 1,10-phenanthroline - phen or 1,4,5,8-tetraazaphenanthrene - TAP). The third ligand was either the heptacyclic heterocycle dipyrido[3,2-a:2',3'-c]quinolino[3,2-h]phenazine (dpqp) substituted at position 12 by an hydroxyl (oxo), 2,2-dimethoxyethylamine (DMEA) or halogeno (Cl or Br) substituent, or the octacyclic dipyrido[3,2-a:2',3'-c]pyrido[2,3,4-de]quinolino[3,2-h]phenazine (dppqp), prepared by a multi-step "chemistry on the complex" strategy from [RuL(oxo-dpqp)](PF). The three steps, halogenation, substitution by a dimethoxyethylamino group and cyclization in trifluoroacetic acid, were performed in reasonable to high yields depending on the nature of the ancillary ligands. Isolation and purification processes were facilitated by the ability to switch the solubility of the complex from aqueous to organic solvents, depending on the counter-ion. All new complexes were fully characterized; in particular their absorption properties were compared by UV-vis spectroscopy. Finally, π-stacking properties induced by these extended ligands were studied by H NMR studies and quantum chemical calculations.

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“…Indeed, position-9 undergoes an 'umpolung', enabling it to act as a nucleo- , as well as bromination or nitration. 62 The Reissert-Henze reaction with trimethylsilyl cyanide and DBU in THF leads to the corresponding 9-cyanoacridine 66d. 63 Acridine N-oxides are much more reactive to various anilines than acridinium salts, and lead to the corresponding 9-(4-aminophenyl) acridine 67a,b in high yields (>90%) (Scheme 22).…”

Section: Reactivity Of N-oxidesmentioning

confidence: 99%

Reactivity of the Acridine Ring: A Review

Chiron¹,

Galy²

2004

Synthesis

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Acridine derivatives are potent biological fluorescent probes, as well as anti-microbial, anti-bacterial, anti-tumor, and DNA-binding agents. The acridinic pattern is included in many therapeutic agents, with more than 600 articles published in 2002 alone. Usual methods for the synthesis of acridines involves the condensation of adequately functionalized anilines and o-halogenobenzoic acid derivatives, or condensation of diphenylamine or diphenylmethane, along with several other steps to give the desired scaffold. However, direct ring functionalization methods are also an interesting synthetic pathway to widely functionalized acridines because they eliminate many synthetic steps and facilitate the synthesis of complex polycyclic structures. This review comprises 138 references that focus on the reactivity of the acridine ring since the publication of Acheson's 1973 book 'The Acridines'. It covers particularly regioselective reactions that occur directly on the acridine ring; these include reduction, electrophilic and nucleophilic additions, and substitutions, as well as radical reactions. 1 Introduction 2 Reduction of the Acridine Ring 3 Reactivity of Position 10 4 Reactivity of Position 9 4.1 Reactivity of Acridines 4.2 Reactivity of Acridiniums 4.3 Reactivity of N-Oxides 5 Reactivity of Positions 4 and 5 6 Reactivity of Positions 1 and 8 7 Reactivity of other Positions 8 Prospects and Conclusion

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673. The bromination and nitration of acridine 10-oxide

Cited by 21 publications

References 0 publications

Extra Coordination of Zn-Tetraphenylporphine with Pyridine, Quinoline, and Acridine N-Oxides

Extra Coordination of Zn-Tetraphenylporphine with Pyridine, Quinoline, and Acridine N-Oxides

Synthesis of three series of ruthenium tris-diimine complexes containing acridine-based π-extended ligands using an efficient “chemistry on the complex” approach

Reactivity of the Acridine Ring: A Review

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