Method for preparing hydroxy-substituted polycyclic aromatic compound

A technology of aromatic compounds and biscarbonyl compounds, applied in the field of organic synthesis

Active Publication Date: 2013-05-01
PEKING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

For naphthol, there is no relatively general synthetic method at present, and the p

Method used

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  • Method for preparing hydroxy-substituted polycyclic aromatic compound
  • Method for preparing hydroxy-substituted polycyclic aromatic compound
  • Method for preparing hydroxy-substituted polycyclic aromatic compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1a

[0030] Example 1a Synthesis of 10-phenyl-9phenanthrene

[0031] Under the protection of argon, add 85.8mg (0.30mmol) of 1,1-biphenyl-2'-benzoyl-2-carboxaldehyde, 58mg (0.309mmol) of p-toluenesulfonate to the dried 25ml Schlenk bottle. Hydrazine, 6ml toluene. After reacting at 70°C for 30 min, NaOMe (41 mg, 0.75 mmol) was added, and the reaction was continued at 70°C for 30 min. AcOH (45mg, 0.75mmol, 2.5eq) was added to the system to quench the reaction and return to room temperature. After the reaction system is concentrated, the product can be obtained by purification with PE / EA=30:1 column chromatography. The reaction formula is as follows:

[0032]

[0033] The obtained compound is a pink solid with a yield of 96%. Its nuclear magnetic data is as follows:

[0034] 1 H NMR(400MHz, CDCl 3 )δ8.67(d, J=7.9Hz, 1H), 8.63(d, J=8.1Hz, 1H), 8.38(d, J=7.9Hz, 1H), 7.69-7.36(m, 10H), 5.45( s, 1H); 13 C NMR(100MHz, CDCl 3 )δ146.03,134.46,132.43,131.42,131.00,129.74,128.56,127.19,126.78,12...

Embodiment 1b

[0035] Example 1b Synthesis of 10-phenyl-9phenanthrene

[0036] Under the protection of argon, add 85.8mg (0.30mmol) of 1,1-biphenyl-2'-benzoyl-2-carboxaldehyde, 58mg (0.309mmol) of p-toluenesulfonate to the dried 25ml Schlenk bottle. Hydrazine, 10ml toluene. After reacting at 70°C for 30 min, NaOMe (41 mg, 0.75 mmol) was added, and the reaction was continued at 70°C for 30 min. AcOH (45mg, 0.75mmol, 2.5eq) was added to the system to quench the reaction and return to room temperature. After the reaction system is concentrated, the product can be obtained by purification with PE / EA=30:1 column chromatography. The reaction formula is as follows:

[0037]

[0038] The obtained compound is a pink solid with a yield of 96%. Its nuclear magnetic data is as follows:

[0039] 1 H NMR(400MHz, CDCl 3 )δ8.67(d, J=7.9Hz, 1H), 8.63(d, J=8.1Hz, 1H), 8.38(d, J=7.9Hz, 1H), 7.69-7.36(m, 10H), 5.45( s, 1H); 13 C NMR(100MHz, CDCl 3 )δ146.03,134.46,132.43,131.42,131.00,129.74,128.56,127.19,126.78,1...

Embodiment 1c

[0040] Example 1c Synthesis of 10-phenyl-9phenanthrene

[0041] Under the protection of argon, add 85.8mg (0.30mmol) of 1,1-biphenyl-2'-benzoyl-2-carboxaldehyde, 58mg (0.309mmol) of p-toluenesulfonate to the dried 25ml Schlenk bottle. Hydrazide, 15ml toluene. After reacting at 70°C for 30 min, NaOMe (41 mg, 0.75 mmol) was added, and the reaction was continued at 70°C for 30 min. AcOH (45mg, 0.75mmol, 2.5eq) was added to the system to quench the reaction and return to room temperature. After the reaction system is concentrated, the product can be obtained by purification with PE / EA=30:1 column chromatography. The reaction formula is as follows:

[0042]

[0043] The obtained compound is a pink solid with a yield of 96%. Its nuclear magnetic data is as follows:

[0044] 1 H NMR(400MHz, CDCl 3 )δ8.67(d, J=7.9Hz, 1H), 8.63(d, J=8.1Hz, 1H), 8.38(d, J=7.9Hz, 1H), 7.69-7.36(m, 10H), 5.45( s, 1H); 13 C NMR(100MHz, CDCl 3 )δ146.03,134.46,132.43,131.42,131.00,129.74,128.56,127.19,126.78,1...

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Abstract

The invention discloses a method for preparing hydroxyl-substituted polycyclic aromatic compound. Dicarbonyl compounds such as intramolecular aldehyde ketone react with sulfohydrazide to obtain single N-sulfonyl-hydrazone, and the single N-sulfonyl-hydrazone reacts in an organic solvent under the alkaline condition, as a result, the hydroxy-substituted polycyclic aromatic compound is obtained. The method utilizes the activity difference between aldehyde and ketone, comprises a procedure of intramolecular carbon-carbon bond insertion-aromatization of the intermediate of the single N-sulfonyl-hydrazone, is short in reaction time and high in reaction yield, can well forbear and universally adapt to functional groups, and can be widely used for preparing various hydroxyl-substituted polycyclic armomatic compounds.

Description

Technical field [0001] The invention belongs to the field of organic synthesis, and particularly relates to a preparation method of polycyclic aromatic compounds. Background technique [0002] Hydroxy-substituted fused-ring aromatic compounds are a very important class of organic compounds. Among them, the polysubstituted compounds on the aromatic ring such as naphthol and phenanthrene are more important to human life and scientific research. Phenanthroline derivatives are a class of natural products that are widely distributed in nature. They are also important intermediates in organic synthesis. They are also an important molecular type in pharmacology, such as antimalarial drugs, anticancer drugs, and anti-HIV. At the same time, the special photochemical and light transmission properties of phenanthrene derivatives make it widely used in material chemistry. Naphthol derivatives are widely used in laboratories and factory industries. They are the basic skeletons of various bio...

Claims

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Application Information

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IPC IPC(8): C07C37/06C07C39/12C07C39/14C07C39/40C07C39/225C07C39/17C07C39/38C07C41/26C07C43/23C07C201/12C07C205/20C07C45/45C07C49/643C07D333/16C07D209/12C07D317/70C07D307/92C07D333/74C07D495/04C07D333/50C07D333/54C07D333/78C07D333/80
Inventor 夏莹曲培源刘振兴葛睿肖卿张艳王剑波
Owner PEKING UNIV
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