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Synthetic process of imidazo phenanthroline compound

A synthesis process and imidazolium technology, applied in the field of new green synthesis process, can solve problems such as a large amount of waste acid, complicated operation, etc., and achieve the effects of avoiding the use of acid, high separation efficiency, and energy-saving production cost.

Active Publication Date: 2013-04-03
ZHEJIANG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But because above-mentioned preparation method is to react in a large amount of sulfuric acid or glacial acetic acid, often produces a large amount of spent acid, and the operation is loaded down with trivial details, and has certain danger

Method used

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  • Synthetic process of imidazo phenanthroline compound
  • Synthetic process of imidazo phenanthroline compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] Add 1,10-phenanthroline-5,6-dione (0.105g, 0.5mmol), ammonium acetate (0.154g, 2mmol) and benzaldehyde (0.0648g, 0.6mmol) successively in a mortar, Grind, make it fully mixed, react at a constant temperature at 85°C for 9 hours, after the reaction is detected by TLC, cool to room temperature, wash with distilled water, adjust pH=7 with concentrated ammonia water, filter with suction, dry, and recrystallize with absolute ethanol to obtain Light yellow powdery solid product (0.1275g, 89.8%): m.p.>300°C (literature value>300°C); 1 H NMR (500MHz, DMSO-d 6 ), δ (ppm): 13.79 (s, 1H, NH), 9.06 (d, J = 1.0Hz, 2H), 8.94 (dd, J1 = 1.0Hz, J 2 =8.0Hz, 2H), 8.33-8.29(m, 2H), 7.90-7.53(m, 5H, ph-H).

Embodiment 2

[0025] Add 1,10-phenanthroline-5,6-dione (0.105g, 0.5mmol), ammonium acetate (0.077g, 1mmol) and benzaldehyde (0.0648g, 0.6mmol) successively in a mortar, Grind, make it fully mixed, react at a constant temperature at 85°C for 9 hours, after the reaction is detected by TLC, cool to room temperature, wash with distilled water, adjust pH=7 with concentrated ammonia water, filter with suction, dry, and recrystallize with absolute ethanol to obtain The product was a pale yellow powdery solid (0.1275 g, 80.5%).

Embodiment 3

[0027] Add 1,10-phenanthroline-5,6-dione (0.105g, 0.5mmol), ammonium acetate (0.154g, 2mmol) and benzaldehyde (0.0648g, 0.6mmol) successively in a mortar, Grind it, make it fully mixed, react at a constant temperature at 60°C for 8 hours, after the reaction is detected by TLC, cool to room temperature, wash with distilled water, adjust pH=7 with concentrated ammonia water, filter with suction, dry, and recrystallize with absolute ethanol to obtain The product was a pale yellow powdery solid (0.1178 g, 74.5%).

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Abstract

The invention discloses a synthetic process of an imidazo phenanthroline compound shown in a formula (III), which comprises the following steps: mixing phenanthroline diketone shown in a formula (I) with aldehyde and ammonium salt shown in a formula (II), and conducting condensation reaction after evenly grinding the mixture, thus obtaining the imidazo phenanthroline compound shown in the formula(III) after complete reaction. In the synthetic process, without the presence of catalyst acid, the synthesis of an imidazole ring is realized by grinding and reacting the phenanthroline diketone with the aldehyde and the ammonium salt under solvent-free conditions, so that the synthetic process has the characteristics of being green and efficient, and is suitable for industrial production.

Description

(1) Technical field [0001] The invention relates to a new green synthesis process for synthesizing imidazophenanthroline compounds by using aldehydes and phenanthroline diketones as raw materials in the presence of ammonium salts. (2) Background technology [0002] Solvent-free organic synthesis is an important direction of green chemistry in recent years, with the advantages of environmental friendliness, high selectivity, easy operation, and mild reaction conditions. Many reactions can be realized by grinding, microwave radiation, ultrasonic wave, oscillation and light, etc. to realize the solvent-free process of reaction, such as asymmetric Aldol condensation, Knoevenagel condensation, Baylis-Hillman reaction, Michael addition reaction and Wittig reaction, etc. got good results. Solvent-free synthesis can greatly simplify the operation and treatment process of the reaction, and has been widely valued by everyone. [0003] Phenanthroline dione and its derivatives have go...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/14
Inventor 李郁锦黄焕明高建荣贾建洪韩亮盛卫坚徐凤双
Owner ZHEJIANG UNIV OF TECH
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