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A kind of efficient and high atom-economical method for synthesizing imidazoline derivatives

An imidazoline derivative and a technology for synthesizing imidazoline, which are applied in the chemical industry, can solve the problems of poor atom economy and substrate compatibility, harsh method conditions and high reaction temperature, and achieve simple purification, simple reaction conditions and strong reaction selectivity. Effect

Active Publication Date: 2021-08-20
FUDAN UNIV
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  • Abstract
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  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The above-mentioned method for synthesizing imidazoline derivatives has harsh conditions, requires the use of oxidants and a large amount of inorganic bases, high reaction temperature, easy to cause side reactions, poor atom economy and substrate compatibility, not energy-saving, environmentally friendly, and post-treatment is more cumbersome

Method used

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  • A kind of efficient and high atom-economical method for synthesizing imidazoline derivatives
  • A kind of efficient and high atom-economical method for synthesizing imidazoline derivatives
  • A kind of efficient and high atom-economical method for synthesizing imidazoline derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] The preparation of 1,4-dimethyl-2-phenylimidazoline has the following structural formula:

[0025]

[0026] Under nitrogen protection, add raw material N-allyl-N-methyl benzamidine (0.5 mmol) and catalyst Y[N(SiMe 3 ) 2 ] 3 (10 mol%), N-methylallylamine (1 mL), reacted at 25 °C for 12 h, and the isolated yield of the product was 96%.

[0027] 1 H NMR (400 MHz, CDCl 3 ): δ 7.54-7.53 (m, 2H), 7.38-7.37 (m, 3H), 4.18-4.09 (m, 1H), 3.57 (t, J = 8.0, 1H), 2.98 (t, J = 8.0 Hz, 1H), 2.76 (s, 3H), 1.32 (d, J = 6.6 Hz, 3H).

Embodiment 2

[0029] The preparation of 1,4-dimethyl-2-p-methylphenylimidazoline has the following structural formula:

[0030]

[0031] Under nitrogen protection, add raw material N-allyl-N-methyl-p-methyl benzamidine (0.5 mmol) and catalyst Y[N(SiMe 3 ) 2 ] 3 (8 mol%), N-methylallylamine (1 mL), reacted at 25 °C for 12 h, and the isolated yield of the product was 85%.

[0032] 1 H NMR (400 MHz, CDCl 3 ): δ 7.45-7.43 (m, 2H), 7.20-7.18 (m, 2H), 4.17-4.08 (m, 1H), 3.57 (t, J = 9.5 Hz, 1H), 2.97 (t, J = 8.7 Hz, 1H ), 2.77 (s,3H), 2.36 (s, 3H), 1.32 (d, J = 6.6 Hz, 3H).

Embodiment 3

[0034] The preparation of 1,4-dimethyl-2-p-chlorophenylimidazoline has the following structural formula:

[0035]

[0036] Under nitrogen protection, add raw material N-allyl-N-methyl p-chlorobenzamidine (0.5 mmol) and catalyst Y[N(SiMe 3 ) 2 ] 3 (10 mol%), N-methylallylamine (1 mL), reacted at 25 °C for 10 h, and the isolated yield of the product was 92%.

[0037] 1 H NMR (400 MHz, CDCl 3 ): δ 7.50-7.48 (m, 2H), 7.38-7.36 (m, 2H), 4.18-4.08 (m, 1H), 3.58 (t, J = 9.5 Hz, 1H), 2.98 (t, J = 8.8 Hz, 1H), 2.76 (s,3H), 1.32 (d, J = 6.6 Hz, 3H).

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Abstract

The invention belongs to the technical field of chemical industry, and specifically relates to a method for synthesizing imidazoline derivatives with high efficiency and high atom economy. The present invention is under rare earth catalytic system, will C‑ Aryl ‑N‑ Allylamidines undergo intramolecular cyclization to imidazolines. The raw materials used in the method of the invention have wide sources or are easy to prepare, are easy to operate, can synthesize imidazoline derivatives with high yield under mild conditions, and have high reaction selectivity.

Description

technical field [0001] The invention belongs to the technical field of chemical industry, and in particular relates to a method for synthesizing imidazoline derivatives. Background technique [0002] Substituted imidazoline rings are important structural units of many natural products and drug molecules. These compounds are not only important intermediates in organic synthesis, but also key precursors for the preparation of functional materials such as imidazolinium salts. In addition, they are also important organic heterocyclic ligands and organic small molecule catalysts. Therefore, the development of new methods for the synthesis of substituted imidazolines with high efficiency and high selectivity is an eternal and important topic in organic synthesis. [0003] In the existing preparation technology, allyl amidine is used as a raw material to prepare imidazoline derivatives through an oxidative ring amidinization reaction method. Literature (J. Am. Chem. Soc., 2011, ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D233/06C07D233/20C07D401/04
CPCC07D233/06C07D233/20C07D401/04
Inventor 周锡庚张德兴刘斌
Owner FUDAN UNIV
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