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Dipyrromethene compound synthetic method

A technology of dipyrrolemethane and a synthesis method, which is applied in the field of synthesis of dipyrrolemethane compounds, can solve the problems of difficult operation, harsh conditions, complicated post-processing process and the like, and achieves a high degree of greening, simple post-processing and low cost. Effect

Inactive Publication Date: 2013-01-02
CHANGCHUN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Most of the reaction conditions are anhydrous and oxygen-free, the conditions are harsh, the operation is difficult, the yield of the target product is 30% to 67%, and the post-treatment process is complicated, relying on cumbersome column chromatography, it is difficult to achieve economical and batch synthesis

Method used

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  • Dipyrromethene compound synthetic method
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  • Dipyrromethene compound synthetic method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0013] Example 1 Add 50 mL of deionized water, 0.5 mL (5 mmol) of benzaldehyde and 2 mL (30 mmol) of pyrrole into a three-necked flask with a dropping device, and the concentration of benzaldehyde in the reaction system is 2 × 10 -3 ~1.4mol / L; purge the solution with nitrogen for 10 minutes to remove oxygen in the water; add 1.4g (0.15mmol) phosphotungstic acid and seal the system, under nitrogen protection, the reaction temperature is 25°C, stir, react for 12 hours, add an appropriate amount of ammonia water The pH of the solution was set at 6.5 to quench the reaction, suction filtered, the filter cake was washed 5 times with distilled water, and vacuum-dried at 40° C. to obtain 0.91 g of 5-phenyldipyrromethane with a yield of 82%.

[0014] The structural characterization data of the product: mp=100°C, 1 H NMR (400MHz, CDCl 3 ): δ5.45(br s, 1H, mesoH), 5.90(m, 2H, 2C 3 -H), 6.14 (dd, 2H, J=2.8, 5.8, 2C 4 -H), 6.67 (br d, 2H, J=2.8, 2C 5 -H), 7.20 (m, 2H, H-Ar), 7.25 (m, 2...

Embodiment 2

[0017] The process conditions of Example 2 are shown in Table 1, and the rest are the same as in Example 1 to obtain 0.65 g of 5-(4-hydroxyphenyl) dipyrromethane with a yield of 55%.

[0018] Structural characterization data of the product: mp = 158°C. 1 HNMR (400MHz, CDCl 3 ): δ5.40(s, 1H, mesoH), 5.90(m, 2H, 2C 3 -H), 6.14 (dd, 2H, J=2.8, 5.8, 2C 4 -H), 6.67(m, 2H, 2C 5 -H), 6.75 (d, 2H, J=8.5, H-Ar), 7.05 (d, 2H, J=8.5, Ar-H), 7.96 (br s, 2H, N-H).

Embodiment 3

[0019] The process conditions of Example 3 are shown in Table 1, and the rest are the same as in Example 1 to obtain 1.3 g of 5-(4-nitrophenyl)dipyrromethane with a yield of 95%.

[0020] Characterization data: mp = 159°C. 1 H NMR (400MHz, CDCl 3 ): δ5.58(s, 1H, mesoH), 5.87(d, 2H, J=5.7Hz, 2C 3 -H), 6.17 (dd, 2H, J=2.8, 5.7, 2C 4 -H), 6.74 (dd, 2H, J=2.8, 1.2, 2C 5 -H), 7.36(d, 2H, J=8.6, H-Ar), 7.98(br s, 2H, N-H), 8.16(d, 2H, J=8.6, Ar-H).

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Abstract

A dipyrromethene compound green synthetic method, especially a synthetic method for pyrrolo Beta-position non-substituted dipyrromethane using pyrrole and aromatic aldehydes and ketones, includes using water as solvent, using pyrrole and aromatic aldehydes and ketones as raw material and phosphotungstic acid as catalyst, and synthesizing dipyrromethane at room temperature in one-step. The dipyrromethane has yield of 44%-95% and purity greater than 99%, and the inventive method avoids the use of organic solvent of greater toxicity and the yield increased by 14%-28%, and it significantly reduces the cost and is batch synthesis process.

Description

technical field [0001] The invention relates to a method for synthesizing dipyrromethane compounds, in particular to a method for synthesizing dipyrromethane compounds using pyrrole and aromatic aldehydes as raw materials. Background technique [0002] Dipyrromethane has a wide range of uses, and can be used as a class of efficient redox catalysts for CO after complexing with metals. 2 reduction of hydrocarbons and oxidation of hydrocarbons; it can also be used to synthesize porphyrin polymers with special photoelectric properties such as liquid crystals 1-5 Precursor of porphyrin photochemotherapy drugs in the synthesis of certain specific spatial structures 6-8 precursor. However, there is still no general method for efficiently synthesizing dipyrromethane. The synthesis of dipyrromethane used in laboratory research mainly adopts the following methods: [0003] [0004] The above-mentioned synthesis method is different according to the kind of organic solvent, and th...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D207/323C07D207/333C07D207/33
Inventor 张龙吴振豪胡江磊
Owner CHANGCHUN UNIV OF TECH
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