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Method for synthesizing benzo[c]pyridine[4,3,2-mn]acridine-8-one

A synthesis method and a benzo-based technology are applied in the field of benzo[c]pyrido[4, homogeneous transition gold catalyzed quinone structure 1, and the effects of readily available raw materials, simple raw materials and mild reaction conditions are achieved.

Inactive Publication Date: 2012-01-18
NANJING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The limitation of this methodology is that the hetero-Diels-Alder reaction typically yields around 30% of the ring-forming product, and simultaneously generates the by-product dihydro-1-azanthraquinone

Method used

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  • Method for synthesizing benzo[c]pyridine[4,3,2-mn]acridine-8-one
  • Method for synthesizing benzo[c]pyridine[4,3,2-mn]acridine-8-one
  • Method for synthesizing benzo[c]pyridine[4,3,2-mn]acridine-8-one

Examples

Experimental program
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Effect test

Embodiment 1

[0020] Example 1: Synthesis of 8H-benzo[c]pyrido[4,3,2-mn]acridin-8-one (II a)

[0021] In a single-necked bottle filled with 2-[3-(2-aminophenyl)-prop-2-ynylamino]naphthoquinone (0.3mmol) and 3.0mL trifluoroacetic acid, stir and add the catalyst triphenylphosphine Gold chloride (4.63mg, 0.015mmol); react at 60°C for 2 hours. It was concentrated under reduced pressure, and chloroform (30 mL) was added to dissolve the concentrate. Then the organic solution was sequentially saturated with water, Na 2 CO 3 Solution wash. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated. The concentrated solution was separated and purified by column chromatography to obtain solid 8H-benzo[c]pyrido[4,3,2-mn]acridin-8-one with a yield of 89%. The reaction temperature can be completed at room temperature, and the reaction time is about long. The same equivalent of gold chloride or sodium chloroaurate can also be used with no significant difference in resul...

Embodiment 2

[0023] Example 2: Synthesis of 3-chloro-8H-benzo[c]pyrido[4,3,2-mn]acridin-8-one (II b)

[0024] The raw materials are 2-[3-(2-amino-5-chloro-phenyl)-prop-2-ynylamino]naphthoquinone 0.3mmol and 3.0mL trifluoroacetic acid; reaction conditions and experimental procedures are as in Example 1 8H-Benzo[c]pyrido[4,3,2-mn]acridin-8-one (II a). 1 HNMR (300MHz, CF 3 CO 2 D) δ9.40-9.33 (m, 2H), 8.99 (d, J=7.5Hz, 1H), 8.83 (s, 1H), 8.52-8.49 (m, 2H), 8.19-7.92 (m, 3H).

Embodiment 3

[0025] Example 3: Synthesis of 3-methyl-8H-benzo[c]pyrido[4,3,2-mn]acridin-8-one (II c)

[0026] The raw materials are 2-[3-(2-amino-5-methyl-phenyl)-prop-2-ynylamino]naphthoquinone 0.3mmol and 3.0mL trifluoroacetic acid; reaction conditions and experimental procedures are as in Example 1 8H-Benzo[c]pyrido[4,3,2-mn]acridin-8-one (II a). 1 HNMR (300MHz, CF 3 CO 2 D) δ9.42(d, J=6.6Hz, 1H), 9.31(d, J=6.6Hz, 1H), 8.83(d, J=7.8Hz, 1H), 8.47(t, J=8.7Hz, 2H ), 8.10 (d, J=8.7Hz, 1H), 8.03-7.94 (m, 2H), 2.65 (s, 3H).

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Abstract

The invention discloses a method for synthesizing benzo[c]pyridine[4,3,2-mn]acridine-8-one. The method comprises the following steps of: performing intramolecular tandem cyclization reaction on 2-[3-(2-amidophenyl)-2-propynylamino]quinone with a 1,5-eneyne structure under the action of a metal catalyst, and purifying to obtain the benzo[c]pyridine[4,3,2-mn]acridine-8-one, wherein R refers to hydroxyl or methoxy; R1 and R2 refer to halogen atoms or alkyl with 1 to 6 carbon atoms; the intramolecular tandem cyclization reaction is homogeneous metal catalysis reaction, and the metal catalyst is gold salt or univalent gold coordination complex; the using amount of the catalyst is equivalent to 0.01 to 0.5 of the quinone raw material; and after the intramolecular tandem cyclization reaction is finished, purification, namely quick column chromatography, is carried out and the benzo[c]pyridine[4,3,2-mn]acridine-8-one is obtained. The raw material is simple and readily available, the reaction conditions are mild, and the chemical regioselectivity is high.

Description

technical field [0001] The invention relates to a homogeneous transition gold catalyzed quinone structure 1,5-enyne series ring formation reaction and a synthesis method of benzo[c]pyrido[4,3,2-mn]acridin-8-one. Background technique [0002] Pyrido[2,3,4-kl]acridin-4-one is an important class of heterocyclic structures; some marine natural alkaloids such as Meridine, Cystodamine, Isocystodamine, Amphimedine and Demethyldeoxyamphimedine contain pyrido[2,3, 4-kl] Acridin-4-ketone structural characteristics (structural formula one); These alkaloid compounds have antitumor cell activity, are a class of potential anticancer drugs (Molinski, T.F.Chem.Rev.1993, 93, 1825.) . [0003] Structural formula one [0004] [0005] Aiming at the structural feature that the A ring in natural alkaloids is pyridine or pyridin-2-one, we imagined that by changing the A ring to a benzene ring or substituting a benzene ring, we synthesized alkaloid analogs to explore the relationship between ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D471/06C07D471/16
Inventor 王少仲尹浩
Owner NANJING UNIV
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