Reactions of π-Deficient Aromatic Heterocycles with Ammonium Polyhalides I. Halogenation of Acridone and Acridine Derivatives Using Benzyltriethylammonium (BTEA) Polyhalides

“…Results and discussions 2,7-Dibromoacridine (2) was synthesized from acridine (1) according to the literature procedure [32] (Scheme 2). This synthetic method selectively gives 2 without any other multibrominated products.…”

Section: Introductionmentioning

confidence: 99%

Herringbone structures of 2,7-dihalogenated acridine tailored by halogen–halogen interactions

Yamamura

Ikuma

Nabeshima

2015

Journal of Molecular Structure

View full text Add to dashboard Cite

“…Commercial reagents were used as received. Ethynylferro- cene, 29 iodoethynylferrocene, 30 10-(2-propynyl)-9-acridone, 16 2-iodoacridone, 31 2,7-dibromoacridine, 31 (11-bromoundecyl)ferrocene, 32 and (8-bromooctyl)ferrocene, 32 34 Cyclic voltammetry in CH2Cl2 and acetone were performed using a three-electrode cell with a polished Pt disk as the working electrode; solutions were ∼10 -3 M in electroactive material and 0.1 M in supporting electrolyte (triply recrystallized TBAPF6). Data were recorded on Powerlab/4sp electrochemical equipment.…”

Section: Methodsmentioning

confidence: 99%

Ethynyl and Ethenyl Ferrocenyl Dyads with Acridine, Acridone, and Anthraquinone

McGale

Robinson

2003

Organometallics

View full text Add to dashboard Cite

Ethynylferrocenyl derivatives of 2,7-acridine (1, 2), 9-N-acridone (4), and 2-anthraquinone (6) are described. (Z)-10-(2-iodo-1-ethenylferrocene)-9(10H)-acridinone (3), an intermediate in the formation of 4, N-Fc(CH2) n -acridone (5; n = 8, 11), 1-Fc-anthraquinone (7), and (E)-(2-FcCC)-anthraquinone (8) were also investigated. The X-ray structures of 3 and 6 were determined. B3LYP calculations, UV/vis spectroelectrochemistry, cyclic voltammetry, and ESR spectra were used to probe the ground and excited states of both the neutral and oxidized compounds. Emission is observed from oxidized, but not neutral, 4 and 6; however, 1, 2, and 8 are fluorescent. Surprisingly, emission is reduced upon oxidation of 2 and 8, which appears to correlate with the greater distortion in the excited compared to ground states.

show abstract

“…In 1995, Vlassa described an efficient method to synthesize selectively 2-halogeno-or 2,7dihalogenoacridine by reacting benzyltriethylammonium (BTEA) polyhalides on acridine. 94 This method was used recently by Kamata with benzyltrimethylammonium tribromide (BTMABr 3 ) and 9-aminoacridine with the same regioselectivity as previously. 95 Ledakrin 123 reacts regioselectively in nucleophilic substitution reactions.…”

Section: Reactivity Of Other Positionsmentioning

confidence: 99%

Reactivity of the Acridine Ring: A Review

Chiron¹,

Galy²

2004

Synthesis

View full text Add to dashboard Cite

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

show abstract

Reactions of π-Deficient Aromatic Heterocycles with Ammonium Polyhalides I. Halogenation of Acridone and Acridine Derivatives Using Benzyltriethylammonium (BTEA) Polyhalides

Cited by 9 publications

References 11 publications

Herringbone structures of 2,7-dihalogenated acridine tailored by halogen–halogen interactions

Herringbone structures of 2,7-dihalogenated acridine tailored by halogen–halogen interactions

Ethynyl and Ethenyl Ferrocenyl Dyads with Acridine, Acridone, and Anthraquinone

Reactivity of the Acridine Ring: A Review

Contact Info

Product

Resources

About