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N-substituted-2-bezilidene-3,4-dihydrobenzo [1,4] oxazine compounds and preparation thereof

A dihydrobenzene and benzylidene technology, applied in the field of organic compounds and synthesis, can solve the problems of low total yield and cumbersome treatment, achieve high conversion rate, optimize the synthesis process, and simplify the post-treatment process

Inactive Publication Date: 2009-05-27
EAST CHINA NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

But all have the following disadvantages: all adopt two-component multi-step reaction, make the post-reaction treatment loaded down with trivial details, multiple separations, purifications have caused the total yield to be low etc.

Method used

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  • N-substituted-2-bezilidene-3,4-dihydrobenzo [1,4] oxazine compounds and preparation thereof
  • N-substituted-2-bezilidene-3,4-dihydrobenzo [1,4] oxazine compounds and preparation thereof
  • N-substituted-2-bezilidene-3,4-dihydrobenzo [1,4] oxazine compounds and preparation thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0022] Example 1: (cis)-2-benzylidene-4-methyl-3,4-dihydrobenzo[1,4]oxazine Synthesis

[0023] 2-(4-methylbenzenesulfonate) phenylmethylamine, phenylacetylene, Paraformaldehyde, dioxane, CuCl, triethylamine, the amount of raw materials is 1.0mmol of 2-(4-methylbenzenesulfonate group) phenylmethylamine, 1.5mmol of phenylacetylene, and 2.0mmol of paraformaldehyde mmol, 3 ml of dioxane, 0.1 mmol of CuCl, and 3.0 mmol of triethylamine were reacted at 110° C. for 20 hours, then potassium hydroxide (10 mmol), 7 ml of ethanol, and 1 ml of water were added, and reacted at 80° C. for 12 hours. 2-(4-Methylbenzenesulfonate group) phenylmethylamine: phenylacetylene: paraformaldehyde: CuCl: triethylamine is 1: 1.5: 2: 0.1: 3, and (cis)-2- Benzylidene-4-methyl-3,4-dihydrobenzo[1,4]oxazine, yield 34%.

[0024] 1 H NMR (CDCl 3 , Me 4 Si) δ 2.76(s, 3H), 3.55(s, 2H), 5.34(s, 1H), 6.64-7.26(m, 7H), 7.60(d, J=8Hz, 2H); 13 C NMR (CDCl 3 , Me 4 Si)δ 38.11, 52.41, 104.55, 112.89, 115.73, 1...

Embodiment 2

[0025] Example 2: (cis)-2-benzylidene-4-methyl-3,4-dihydrobenzo[1,4]oxazine Synthesis

[0026] 2-(4-methylbenzenesulfonate) phenylmethylamine, phenylacetylene, Paraformaldehyde, dioxane, CuCl, triethylamine, the amount of raw materials is 1.0mmol of 2-(4-methylbenzenesulfonate group) phenylmethylamine, 1.5mmol of phenylacetylene, and 2.0mmol of paraformaldehyde mmol, 3ml of dioxane, 0.15mmol of CuCl, 3.0mmol of triethylamine, reacted at 110°C for 20 hours, then added potassium hydroxide (10mmol), 7ml of ethanol, and 1ml of water, and reacted at 80°C for 12 hours, 2-(4-methylbenzenesulfonate group) phenylmethylamine: phenylacetylene: paraformaldehyde: CuCl: triethylamine is 1: 1.5: 2: 0.15: 3, and (cis)-2- Benzylidene-4-methyl-3,4-dihydrobenzo[1,4]oxazine, the yield is 60%.

Embodiment 3

[0027] Example 3: (cis)-2-benzylidene-4-methyl-3,4-dihydrobenzo[1,4]oxazine Synthesis

[0028] 2-(4-methylbenzenesulfonate) phenylmethylamine, phenylacetylene, Paraformaldehyde, dioxane, CuCl, triethylamine, the amount of raw materials is 1.0mmol of 2-(4-methylbenzenesulfonate group) phenylmethylamine, 1.5mmol of phenylacetylene, and 2.0mmol of paraformaldehyde mmol, 3ml of dioxane, 0.2mmol of CuCl, 3.0mmol of triethylamine, reacted at 110°C for 20 hours, then added potassium hydroxide (10mmol), 7ml of ethanol, and 1ml of water, and reacted at 80°C for 12 hours, 2-(4-Methylbenzenesulfonate) phenylmethylamine: phenylacetylene: paraformaldehyde: CuCl: triethylamine is 1: 1.5: 2: 0.2: 3, to get (cis)-2- Benzylidene-4-methyl-3,4-dihydrobenzo[1,4]oxazine, the yield is 85%.

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Abstract

The invention relates to a N-substituted-2-toluenyl-3, 4-dihydrobenzo[1,4]oxazine compound and a synthesis method, which belong to the technical field of organic compound and the synthesis. The method for preparing the compound comprises the following steps: an ortho-4-methyl benzene sulfonate substituted aniline compound, substituted aryl alkyne and paraformaldehyde are taken as raw materials, and copper salt is taken as a catalyst to synthesize the N-substituted-2-toluenyl-3, 4-dihydrobenzo[1,4]oxazine compound. The method has the advantages of simple and easily-obtained raw materials, simple and convenient post-treatment, cheap catalyst and high yield.

Description

technical field [0001] The invention relates to N-substituted-2-benzylidene-3,4-dihydrobenzo[1,4]oxazine compounds and a synthesis method, belonging to the technical field of organic compounds and synthesis. Background technique [0002] 3,4-dihydro-benzo[1,4]oxazines (3,4-dihydro-1,4-benzoxazines) are an important class of heterocyclic compounds. These compounds have a variety of medicinal value and biological activity, and are important structural units of many natural products. The synthesis of 3,4-dihydrobenzo[1,4]oxazines has been reported in the literature. However, there are few reports on functionalized 3,4-dihydrobenzo[1,4]oxazine compounds and their synthesis methods. The limitation of the reported methods is that they all use two-component multi-step reactions. The two-component multi-step synthesis of 3,4-dihydrobenzo[1,4]oxazines has been reported: Literature (1) Kundu, N.; Chaudhuri, G.; Upadhyay, A.J.Org.Chem. 2001,66,20; and (2) Bunce, R.; Merron, D.; Yale...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D265/36
Inventor 李艳忠王二捐徐晓冰梁淋峰刘俊
Owner EAST CHINA NORMAL UNIV
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