Cyclopenta[c]chromene compound and preparation method thereof

A technology of chromene compound and cyclopentadiene, which is applied in the field of cyclopenta[c]chromene compound and its preparation, can solve the problems of complex substrate, lack of research, low yield, etc., and achieve simple reaction process , low reaction cost and high yield

Active Publication Date: 2021-12-17
ZHANGJIAGANG INST OF IND TECH SOOCHOW UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The common feature of these synthetic routes is that the required substrates are relatively complex, mostly involving aryl monoynes and diynes, and often require the participation of noble metals or metering bases, and the yields are mostly low, so there are certain limitations.
What is particularly prominent is that only a few of these methods can obtain cyclopenta[c]chromene compounds, and most of the synthetic methods finally obtain indeno[c]chromene compounds, so the research on the synthesis of the former is very important. lacking

Method used

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  • Cyclopenta[c]chromene compound and preparation method thereof
  • Cyclopenta[c]chromene compound and preparation method thereof
  • Cyclopenta[c]chromene compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Embodiment one: Catalyst [Yb(CH 3 EN) 9 ] 3+ [(AlCl 4 ) 3 ] 3– •CH 3 Synthesis of CN

[0036] In the reaction flask that has been dehydrated and deoxygenated, weigh 0.70 g (2.5 mmol) of YbCl at a molar ratio of 1:3 under the protection of argon. 3 and 1.00 g (7.5 mmol) of anhydrous AlCl 3 , add 25 mL of acetonitrile to dissolve, stir at room temperature for 24 hours, centrifuge, take the supernatant, concentrate and put it in a refrigerator at 0°C, the obtained crystal is [Yb(CH 3 EN) 9 ] 3+ [(AlCl 4 ) 3 ] 3– •CH 3 CN, the yield is 46%.

[0037] Other [Ln(CH 3 EN) 9 ] 3+ [(AlCl 4 ) 3 ] 3– •CH 3 The CN catalyst can be prepared by referring to the method of Example 1, replacing the rare earth chloride.

Embodiment 2

[0038] Embodiment two: [Yb(CH 3 EN) 9 ] 3+ [(AlCl 4 ) 3 ] 3– •CH 3CN Catalyzed Reaction of 2-Hydroxychalcones to Prepare Cyclopenta[c]Chromene Compounds

[0039] In the reaction flask treated with dehydration and deoxygenation, weigh [Yb(CH 3 EN) 9 ] 3+ [(AlCl 4 ) 3 ] 3– •CH 3 CN (0.0163 g, 0.015 mmol, 3 mol%), added 2-hydroxychalcone (0.1121 g, 0.5 mmol) and chlorobenzene (1 mL), stirred for 2 minutes, added 2-naphthylthiol (0.0961 g, 0.6 mmol) and chlorobenzene (1 mL), mixed well, stirred and refluxed for 24 hours, added water to terminate the reaction, extracted three times with ethyl acetate (10 mL × 3), dried the extract with anhydrous sodium sulfate, filtered, and removed the solvent under reduced pressure. Finally, flash column chromatography on a silica gel column (eluent: V 乙酸乙酯 :V 石油醚 = 1:20~1:15) to obtain a reddish-brown solid, which was placed under an oil pump and continued to be vacuumed for about one day, with a yield of 46%.

[0040] The theor...

Embodiment 3

[0043] Embodiment three: [Yb(CH 3 EN) 9 ] 3+ [(AlCl 4 ) 3 ] 3– •CH 3 CN Catalyzed Reaction of 2-Hydroxychalcones to Prepare Cyclopenta[c]Chromene Compounds

[0044] In the reaction flask treated with dehydration and deoxygenation, weigh [Yb(CH 3 EN) 9 ] 3+ [(AlCl 4 ) 3 ] 3– •CH 3 CN (0.0381 g, 0.035 mmol, 7 mol%), add 2-hydroxychalcone (0.1121 g, 0.5 mmol) and chlorobenzene (1 mL), stir for 2 minutes, continue to add 2-naphthylthiol (0.0961 g, 0.6 mmol) and chlorobenzene (1 mL), mix well, stir and reflux for 24 hours, add water to terminate the reaction, extract three times with ethyl acetate (10 mL × 3), dry the extract with anhydrous sodium sulfate, filter, and remove the solvent under reduced pressure , and finally flash column chromatography on a silica gel column (eluent: V 乙酸乙酯 :V 石油醚 = 1:20~1:15) to obtain a reddish-brown solid, which was placed under an oil pump and continued to be vacuumed for about one day, with a yield of 87%.

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PUM

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Abstract

The invention discloses a cyclopentadiene [c] chromene compound and a preparation method thereof. The cationic rare earth compound [Ln(CH 3 EN) 9 ] 3+ [(AlCl 4 ) 3 ] 3– •CH 3 CN is a catalyst, 2-naphthylthiol is a promoter, and catalyzes the reaction of chalcone compounds to prepare products; Ln in the catalyst represents positive trivalent rare earth metal ions, selected from one of La, Nd, Sm, Gd, and Yb. In this method, raw material is easy to obtain, and reaction process is simple, and the consumption of catalyst is few; Catalyst has universal applicability to multiple substituted 2-hydroxychalcones, and the obtained cyclopentadien[c]chromene compound has no See the report; the catalyst synthesis method is simple and easy to obtain; the yield of the target product is high, up to 85%.

Description

technical field [0001] The invention belongs to the technical field of preparation of organic oxa-fused ring compounds, and in particular relates to a cyclopenta[c]chromene compound and a preparation method thereof. Background technique [0002] Cyclopenta[c]chromene is an important class of oxa-fused ring compounds. Most of the compounds containing cyclopenta[c]chromene structure have good biological activity, and cyclopenta[c]chromene is also the synthesis of many biologically active natural products (such as 11-oxa steroids) important precursor. Therefore, it is of great theoretical and practical significance to develop efficient methods for the synthesis of cyclopenta[c]chromene skeletons. [0003] In the prior art, the reported synthesis routes of cyclopenta[c]chromene skeletons are relatively limited, and the main routes used include: hetero[6+3] of 1,6-dimethylaminofulvene and benzoquinone Cycloaddition reactions (see Hong, B.; Chen, Z.; Chen, W. Org. Lett. 2000, ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D311/94B01J31/22
CPCC07D311/94B01J31/1805
Inventor 徐凡丁晓友李丹丹朱亚楠姚志刚
Owner ZHANGJIAGANG INST OF IND TECH SOOCHOW UNIV
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