Regiospecific synthesis of quinizarin derivatives by cycloaddition

Cameron, Donald W.; Feutrill, G. I.; McKay, Peter G.

doi:10.1016/s0040-4039(01)92528-6

Cited by 7 publications

(2 citation statements)

References 10 publications

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“…Anthraquinones. The synthesis and characterization of 1,5-dimethoxyanthraquinone (15MAQ) and 1,4-dimethoxyanthraquinone (14MAQ) were reported previously. ,, …”

Section: Methodsmentioning

confidence: 99%

“…The synthesis and characterization of 1,5-dimethoxyanthraquinone (15MAQ) and 1,4-dimethoxyanthraquinone (14MAQ) were reported previously. 7,19,20 1,5-Bis(2-methoxyethoxy)anthraquinone (EOAQ). 2-Methoxyethanol (9.9 mmol, 0.75 g) was added dropwise to a stirred slurry of sodium hydride (9.9 mmol, 0.23 g) in 25 mL of THF, and the mixture was heated in an oil bath at 65 °C for 45 min.…”

Section: Methodsmentioning

confidence: 99%

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Novel Polyaromatic Quinone Imines. 2. Synthesis of Model Compounds and Stereoregular Poly(quinone imines) from Disubstituted Anthraquinones

Boone

Hall

1996

Macromolecules

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Novel poly(quinone diimines) from anthraquinones symmetrically disubstituted with solubilizing ethyleneoxy or long chain alkoxy groups have been synthesized and characterized. The disubstituted anthraquinones 1,5-bis(2-methoxyethoxy)anthraquinone (EO1AQ), 1,5-bis(2-(2-methoxyethoxy)ethoxy)anthraquinone (EO2AQ), 1,5-bis(2-(2-(2-methoxyethoxy)ethoxy)anthraquinone (EO2AQ), 1,5-bis(2-(2-2-methoxyethoxy)ethoxy)ethoxy)anthraquinone (EO3AQ), 1,5-bis(octyloxy)anthraquinone (15OOAQ), 2,6-bis(octyloxy)anthraquinone (26OOAQ), and 1,4-bis(octyloxy)anthraquinone (14OOAQ) were synthesized and condensed with aniline in the presence of titanium tetrachloride and 1,4-diazabicyclo[2.2.2]octane to give N,N‘-diphenyl-1,5-bis(2-methoxyethoxy) n anthraquinone 9,10-diimine (DEO n AQ, n = 1−3), N,N-diphenyl-1,5-bis(octyloxy)anthraquinone 9,10-diimine (15DOOAQ), and N,N‘-diphenyl-2,6-bis(octyloxy)anthraquinone 9,10-diimine (26DOOAQ), respectively, as model compounds for the polymers. The relative stereochemistry of these diimines was determined by 1H NMR spectroscopy. Polycondensation of the disubstituted anthraquinones with 4,4‘-thiodianiline (SDA) gave high molecular weight (M w 30 000) poly(anthraquinone diimines) and large macrocycles. Polycondensation of 1,4-phenylenediamine (PDA) with EO2AQ gave high molecular weight (M w 14 000) polyaromatic anthraquinone diimines. PDA gave molecular weights of M w 5000−23 000 for the bis(octyloxy)-substituted anthraquinones. The molecular weights of polymerizations incorporating PDA are lowered due to steric interactions of successive repeat units and solubility constraints.

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“…Anthraquinones. The synthesis and characterization of 1,5-dimethoxyanthraquinone (15MAQ) and 1,4-dimethoxyanthraquinone (14MAQ) were reported previously. ,, …”

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%