Synthesis of Anthrapyrimidine Derivatives

Nishio, K; Kasai, T.; Tsuruoka, Subaru

doi:10.1246/nikkashi1898.71.12_2026

Cited by 4 publications

(5 citation statements)

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“…Preparation of 1 H ,7 H -Benzo[ e ]perimidin-2,7-dione (14c) . This was prepared from 11 and urea by a literature procedure 23 as a brown solid, mp >316 °C (lit . mp >360 °C).…”

Section: Methodsmentioning

confidence: 99%

“…The resulting 3 H ,7 H -dibenz[ f,ij ]isoquinoline-2,7-dione ( 14b ) reacted readily with phosphoryl chloride, converting the 2-oxo function to give the chloro compound 15a . Reaction of 11 with urea in hot phenol gave 1 H, 7 H -benzo[ e ]perimidine-2,7-dione ( 14c ). Again, the related chloro compound 15b was formed by reaction with phosphoryl chloride.…”

Section: Chemistrymentioning

confidence: 99%

“…This was prepared from 11 and urea by a literature procedure23 as a brown solid, mp >316 °C (lit 23. mp >360 °C).…”

mentioning

confidence: 99%

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Synthesis and Cytotoxic Activity of 7-Oxo-7H-dibenz[f,ij]isoquinoline and 7-Oxo-7H-benzo[e]perimidine Derivatives

Deady

Finlay

et al. 2001

J. Med. Chem.

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A series of 7-oxo-7H-dibenz[f,ij]isoquinoline and 7-oxo-7H-benzo[e]perimidines bearing cationic side chains were prepared from aminoanthraquinones. The perimidines were prepared from 1-aminoanthraquinone by initial condensation with urea or dimethylacetamide. A series of 2-, 4-, 8-, and 11-carboxy derivatives of the dibenzisoquinolines were prepared from aminoanthraquinonecarboxylic acids. The cationic derivatives were prepared from these via amide, amine, or methylene linkers to study the effects of side chain positioning on biological activity. Within the series of carboxamide-linked compounds, the order of increasing cytotoxicity was 8- < 4- < 2- < 11-. The 2- and 4-carboxamides showed substantial growth delays against in vivo subcutaneous colon 38 tumors in mice, but the 11-carboxamide had curative activity in this refractory model and is being investigated further.

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“…Preparation of 1 H ,7 H -Benzo[ e ]perimidin-2,7-dione (14c) . This was prepared from 11 and urea by a literature procedure 23 as a brown solid, mp >316 °C (lit . mp >360 °C).…”

Section: Methodsmentioning

confidence: 99%

Section: Chemistrymentioning

confidence: 99%

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Synthesis and Cytotoxic Activity of 7-Oxo-7H-dibenz[f,ij]isoquinoline and 7-Oxo-7H-benzo[e]perimidine Derivatives

Deady

Finlay

et al. 2001

J. Med. Chem.

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“…Anthrapyrimidine colorants are characterised by exceptionally good heat stability and fastness properties and hence are used for the coloration of polymers [1]. Cyclisation in ethanol in the presence of ammonium acetate ⁄ formate gives the desired product [6][7][8]. They were also used as luminescent dyestuffs and fluorols, giving bright fluorescent green shades on polyesters [4].…”

Section: Introductionmentioning

confidence: 99%

“…A newly developed, simpler route proceeds via formamidinium chloride, which is prepared from 1‐aminoanthraquinone with N , N ‐dimethylformamide (DMF) and thionyl chloride or phosphorus oxychloride. Cyclisation in ethanol in the presence of ammonium acetate/formate gives the desired product [6–8].…”

Section: Introductionmentioning

confidence: 99%

The synthesis, photophysical and thermal properties of new anthrapyrimidine colorants

Menon

Shankarling

2011

Coloration Technology

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The thermal and photostability of novel anthrapyrimidine-containing colorants obtained by the condensation of various substituted aromatic amines with 6-bromo-7H-benzo[e]perimidin-7-one are described. The colorants were characterised by proton nuclear magnetic resonance, elemental analysis and mass spectra. Thermogravimetric analysis showed that these colorants are thermally stable up to 250°C. The UV-visible absorption spectra of the colorants were studied in solvents of differing polarity; the colorants exhibited slight positive solvatochromism. The photostability studies in dimethyl sulphoxide solvent were recorded by monitoring photodegradation of the colorants spectrophotometrically using a standard calibration curve. All the colorants exhibited excellent photostability. The light fastness study of two colorants in polypropylene showcases their ability as useful colorants for plastics.

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Anthraquinonoid Vat Dyes

Венкатараман

Iyer

1971

The Chemistry of Synthetic Dyes

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Synthesis of Anthrapyrimidine Derivatives

Cited by 4 publications

References 0 publications

Synthesis and Cytotoxic Activity of 7-Oxo-7H-dibenz[f,ij]isoquinoline and 7-Oxo-7H-benzo[e]perimidine Derivatives

Synthesis and Cytotoxic Activity of 7-Oxo-7H-dibenz[f,ij]isoquinoline and 7-Oxo-7H-benzo[e]perimidine Derivatives

The synthesis, photophysical and thermal properties of new anthrapyrimidine colorants

Anthraquinonoid Vat Dyes

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