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Synthetic method of 12-phenyl-benzo[b] xanthenetrione derivative

A synthesis method and xanthene technology, applied in organic chemistry and other directions, can solve problems such as complex reaction process, and achieve the effects of simple separation, unique solubility and cost reduction.

Inactive Publication Date: 2011-12-14
XUZHOU NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The above synthesis method requires the use of a catalyst to catalyze the reaction or the use of a special reaction device, and the reaction process is complicated
In ionic liquid, 3,4-dihydro-12-phenyl-2H-benzo[b ]xanthene-1,6,11(12H)-trione derivatives have not been reported

Method used

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  • Synthetic method of 12-phenyl-benzo[b] xanthenetrione derivative
  • Synthetic method of 12-phenyl-benzo[b] xanthenetrione derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0013] Preparation of 3,4-dihydro-3,3-dimethyl-12-(4-chlorophenyl)-2H-benzo[b]xanthene-1,6,11(12H)-trione: In 5 mL of ionic liquid [Bmim]Br were added 1 mmol of 4-chlorobenzaldehyde (0.14 g), 1 mmol of 2-hydroxy-1,4-naphthoquinone (0.17 g) and 1 mmol of 5, 5-Dimethyl-1,3-cyclohexanedione (0.14g), reacted at 90°C for 9 hours, followed by TLC monitoring, after the reaction, directly filtered, the product was washed with a small amount of water, dried with DMF / H 2 O recrystallization to obtain the corresponding 3,4-dihydro 12-phenyl-2H-benzo[b]xanthene-1,6,11(12H)-triketone derivatives (0.36g, yield 86 %). This product is khaki powder, mp: 247~248℃.

Embodiment 2

[0015] Preparation of 3,4-dihydro-3,3-dimethyl-12-(2-bromophenyl)-2H-benzo[b]xanthene-1,6,11(12H)-trione: In 5 mL of ionic liquid [Bmim]Br were added 1 mmol of 2-bromobenzaldehyde (0.19 g), 1 mmol of 2-hydroxy-1,4-naphthoquinone (0.17 g) and 1 mmol of 5, 5-Dimethyl-1,3-cyclohexanedione (0.14g), reacted at 90°C for 8 hours, followed by TLC monitoring, after the reaction, directly filtered, the product was washed with a small amount of water, dried with DMF / H 2 O recrystallization promptly obtains corresponding 3,4-dihydro 12-(2-bromophenyl)-2H-benzo[b]oxanthene-1,6,11(12H)-triketone derivatives (0.38 g, yield 82%). This product is yellow powder, mp: 275~277℃.

Embodiment 3

[0017] Preparation of 3,4-dihydro-12-(4-chlorophenyl)-2H-benzo[b]xanthene-1,6,11(12H)-trione: in 5 mL of ionic liquid [Bmim] Add 1 mmol of 4-chlorobenzaldehyde (0.14 g), 1 mmol of 2-hydroxy-1,4-naphthoquinone (0.17 g) and 1 mmol of 1,3-cyclohexanedione (0.11 g) to Br. g), reacted at 90°C for 9 hours, followed by TLC monitoring, after the reaction, directly filtered, the product was washed with a small amount of water, dried with DMF / H 2 O recrystallization promptly obtains corresponding 3,4-dihydro-12-phenyl-2H-benzo[b]oxanthene-1,6,11(12H)-triketone derivatives (0.35g, yield 89%). This product is brown powder, mp: 210-212℃.

[0018] See Table 1 for the reaction raw materials, reaction conditions and yields of Examples 1-21.

[0019] The reaction raw material of table 1 embodiment 1-21, reaction condition and productive rate

[0020]

[0021] In Table 1, the cyclic 1,3-dicarbonyl compound reacted in Examples 1-14 is 5,5-dimethyl-1,3-cyclohexanedione, and the cyclic 1 re...

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Abstract

The invention relates to the synthesis of a 12-phenyl-benzo[b] xanthenetrione derivative, and especially relates to the synthesis of 3, 4-dihydro-12-phenyl-2H-benzo[b] xanthene -1, 6, 11 (12H)-trione, which is produced by subjecting the raw materials of aldehyde, 2-hydroxy-1, 4-naphthoquinone and an annular 1, 3-dicarbonyl compound to a one-step reaction by a three component one-pot synthesis method. With simple synthetic process and mild condition, the method of the invention has an overall yield over 80%.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis and relates to an organic synthesis method of 3,4-dihydro-12-phenyl-2H-benzo[b]xanthene-1,6,11(12H)-trione. Background technique [0002] Benzo[b]xanthenes are a class of heterocyclic compounds with important physiological and pharmacological activities. It has antimicrobial, anti-inflammatory, antibacterial and other activities. This class of compounds can be used as dyes for laser technology and pH-sensitive fluorescent substances as chromogens for biomolecules. Therefore, benzo[b]xanthene derivatives have always been a focus of attention of chemists and pharmaceutical scientists. The 1,4-naphthoquinone structure is also a widespread structural unit in natural products with antifungal, antimicrobial and anticancer activities. However, there are few reports on the synthesis of benzo[b]xanthene derivatives with 1,4-naphthoquinone structure. It has been reported in the literature that...

Claims

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Application Information

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IPC IPC(8): C07D311/02
Inventor 李玉玲杜百祥
Owner XUZHOU NORMAL UNIVERSITY
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