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A kind of method for preparing imidazolin-2 ketone compound

A ketone compound, imidazoline technology, applied in the field of imidazoline-2 ketone compounds, can solve the problems of limited nitrogen source, environmental pollution, increased cost, etc., and achieves the effects of good atom economy and step economy.

Active Publication Date: 2019-10-29
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

Although there are many methods for synthesizing such compounds, there are still many problems, such as these methods usually require the participation of stoichiometric or catalytic amounts of expensive transition metal catalysts and oxidants, which increases additional costs and causes environmental pollution, and Nitrogen sources are also relatively limited

Method used

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  • A kind of method for preparing imidazolin-2 ketone compound
  • A kind of method for preparing imidazolin-2 ketone compound
  • A kind of method for preparing imidazolin-2 ketone compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0020]

[0021] Compound 1 (53 mg, 0.5 mmol) and compound 2 (187 mg, 1 mmol, 2 equiv) were dissolved in anhydrous tetraglyme (tetraethylene glycol dimethyl ether), heated at 250 ° C for 0.5 hours, after the solvent was cooled, added Ethyl acetate, washed the organic layer three times with water, combined the aqueous layer, washed the aqueous layer once with the ethyl acetate layer, combined the organic layers, washed with saturated brine, dried over anhydrous sodium sulfate, evaporated to dryness, and purified by column chromatography , the product 4 was obtained with a yield of 20%. 1 H NMR (400 MHz, CDCl 3 ): δ7.65 (s, 2H), 7.56 (d, J = 8.4 Hz, 2H), 7.38 (d, J = 8.1 Hz, 2H), 6.23 (d, J = 9.4 Hz, 2H), 5.34 (dd, J = 14.9, 6.9 Hz, 2H), 2.58 (t, J = 6.3 Hz, 2H). 13 CNMR (151 MHz, CDCl 3 ): δ 150.38, 134.11, 133.36, 131.55, 131.02, 127.65, 125.09, 124.43, 116.78, 116.75, 28.22. LR-MS (ESI): m / z 436.9 [M+H] + .

[0022] Compound 1 (53 mg, 0.5 mmol) and compound 2 (...

Embodiment 2

[0027] Compound 1 (53 mg, 0.5 mmol) and compound 2 (187 mg, 1 mmol, 2 equiv) were dissolved in anhydrous triglyme (triethylene glycol dimethyl ether), heated at 180 °C for 1 hour, after the solvent was cooled, added Ethyl acetate, washed the organic layer three times with water, combined the aqueous layer, washed the aqueous layer once with the ethyl acetate layer, combined the organic layers, washed with saturated brine, dried over anhydrous sodium sulfate, evaporated to dryness, and purified by column chromatography , the product 4 was obtained with a yield of 82%.

Embodiment 3

[0029]

[0030] Compound 1 (53 mg, 0.5 mmol) and compound 5 (288 mg, 2 mmol, 4 equiv) were dissolved in anhydrous triethylene glycol dimethyl ether, heated at 180 °C for 1 hour, after the solvent was cooled, ethyl acetate was added , washed the organic layer 3 times with water, combined the aqueous layer, washed the aqueous layer once with the ethyl acetate layer, combined the organic layer, washed with saturated brine, dried over anhydrous sodium sulfate, evaporated to dryness by rotary evaporation, and purified by column chromatography to obtain the product 6. The yield is 89%. 1 H NMR (400 MHz, CDCl 3 ): δ 7.82 (d, J =9.3 Hz, 4H), 7.68–7.58 (m, 4H), 6.22 (d, J = 9.4 Hz, 2H), 5.38 (dd, J = 15.6,7.2 Hz, 2H), 2.62 (t, J = 6.7 Hz, 2H). 13 C NMR (151 MHz, CDCl 3 ): δ 150.39,135.64, 130.86, 130.42, 130.04, 128.89, 124.37, 117.98, 117.34, 116.63,113.63, 28.20. LR-MS (ESI): m / z 351.1.

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Abstract

The invention discloses a method for preparing an imidazoline-2 ketone compound. The method comprises the following steps: dissolving tropone and aryl isocyanate into a water-free solvent, and reacting for 0.5-5 hours at a temperature being 160-200 DEG C; extracting, drying by distillation after reaction is completed, and performing column chromatography and purifying to obtain a product imidazoline-2 ketone compound. The method is a simple method for synthesizing the imidazoline-2 ketone compound, does not need an oxidant and a metal catalyst, is simpler in comparison with a conventional alpha-amino carbonyl compound or propargyl urea compound, is good in atomic economical efficiency and is good in step economical efficiency.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, in particular to the reaction of isocyanate and cycloheptatrienone to prepare imidazoline-2 ketone compounds. Background technique [0002] Imidazolin-2 ketones are a very important part of ortho-diamine derivatives. Many biologically active molecules and synthetic intermediates contain imidazolin-2 ketone structures, such as dopamine D4 receptor antagonists, MurB inhibitors. , CGRP receptor antagonists and many antitumor drugs contain this structure. Conventionally, the synthesis of imidazolin-2 ketone compounds is usually carried out by cyclization of compounds such as α-aminocarbonyl compounds or propargyl ureas. Although there are many methods for synthesizing such compounds, there are still many problems, such as these methods usually require the participation of stoichiometric or catalytic amounts of expensive transition metal catalysts and oxidants, which increases additional co...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D235/02
CPCC07D235/02
Inventor 张士磊刘晔蒋静毛玉健胡延维陈韶华
Owner ZHANGJIAGANG INST OF IND TECH SOOCHOW UNIV