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Structure and preparation method for heterocyclic aryl acetylene compounds containing benzoxazole and benzothiazole groups

A technology of benzothiazolyl and benzoxazole, applied in the field of heteroaryl acetylene compounds, can solve problems such as difficulty in obtaining raw materials, high price and the like

Inactive Publication Date: 2012-09-12
BEIJING UNIV OF CHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0036] This type of reaction is a coupling reaction using metal as a catalyst. The selected raw materials are not easy to obtain and are expensive. These methods are mostly suitable for theoretical research on methodology

Method used

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  • Structure and preparation method for heterocyclic aryl acetylene compounds containing benzoxazole and benzothiazole groups
  • Structure and preparation method for heterocyclic aryl acetylene compounds containing benzoxazole and benzothiazole groups
  • Structure and preparation method for heterocyclic aryl acetylene compounds containing benzoxazole and benzothiazole groups

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] Embodiment 1, the synthesis of 1-phenyl-2-(2-benzoxazolyl)acetylene and its derivatives

[0047] A. Synthesis of Heteroaryl Vinyl Compounds

[0048] The raw material heteroaryl vinyl compound of the heteroaryl acetylene compound containing benzoxazole group is synthesized according to the method in the literature. [W. Q. Zhang, J. P. Zhuang, et al., Chinese J. Chem., 2001, 19 (7): 695-701] using substituted aromatic aldehydes as raw materials and 2-methylbenzoxazole as raw materials, with N, N-dimethylformamide is used as a solvent and potassium hydroxide is used as a base catalyst to obtain the target compound.

[0049]

[0050] Weigh 10.61g (0.10mol) of benzaldehyde, 13.32g (0.10mol) of 2-methylbenzoxazole, 150mL of DMF, and 15g of KOH, and add them to a 500mL round-bottomed flask, and stir at room temperature for 2 hours before TLC detection , the reaction is complete. The solution was added to 800mL of water, and a large amount of yellow precipitate was precip...

Embodiment 2

[0069] Embodiment two, the synthesis of 1-phenyl-2-(2-benzothiazolyl) acetylene and its derivatives

[0070] A. Synthesis of benzothiazole-containing heteroaryl vinyl compounds

[0071]

[0072] The synthesis of heteroaryl vinyl compounds containing benzothiazole groups is similar to the synthesis method of heteroaryl vinyl compounds containing benzoxazole groups in Example 1, and the yields are as follows.

[0073] 1-Phenyl-2-(2-benzothiazolyl)ethene, yield: 87.2%

[0074] 1-(4-chlorophenyl)-2-(2-benzothiazolyl)ethylene, yield: 95.4%

[0075] 1-(4-bromophenyl)-2-(2-benzothiazolyl)ethylene, yield: 90.6%

[0076] 1-(4-methylphenyl)-2-(2-benzothiazolyl)ethylene, yield: 95.4%

[0077] B, synthesis of benzothiazole-containing heteroarylethene compound brominated product

[0078]

[0079] Weigh 12.37g (0.052mol) of 1-phenyl-2-(2-benzothiazolyl)ethylene into a 250mL round bottom flask, add 100mL of dichloromethane and stir to dissolve, add dropwise 8.90g of liquid bromine ...

Embodiment 3 1

[0095] Embodiment three, the synthesis of 1,2-two (2-benzoxazolyl) acetylene

[0096] The synthesis of 1,2-bis(2-benzoxazolyl)ethylene refers to the literature, and it is prepared by reacting o-aminophenol and butenedioic acid under the condition of polyphosphoric acid as a solvent. [E.V. Paul, H. Julia, et al. WO 02 / 32886A1]

[0097]

[0098] A, 1, the synthesis of 2-bis(2-benzoxazolyl)-1-bromoethylene

[0099] Take the above 5.00g (0.019mol) 1,2-bis(2-benzoxazolyl)ethylene in a 500°C round bottom flask, add 250ml of dichloromethane, heat to reflux, cool to room temperature, take 3.07g (0.019mol ) liquid bromine into the constant pressure dropping funnel, the dropwise addition was completed in about one hour, stirred at room temperature for 5 hours, and then refluxed overnight, a large amount of precipitate was formed, the heating device was removed, and the crude product was obtained by spinning. Due to the poor solubility of the crude product, only a small amount was t...

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Abstract

The invention discloses a structure and a preparation method for heterocyclic aryl acetylene compounds containing benzoxazole and benzothiazole groups. The preparation method comprises the following steps: reacting heterocyclic aryl acetylene compounds containing benzoxazole and benzothiazole groups with bromine in an organic solvent to obtain brominized products; and reacting with alkali in the organic solvent, and removing hydrogen bromide to obtain the heterocyclic aryl acetylene compounds.

Description

Technical field: [0001] The invention uses the heteroaryl vinyl compounds containing benzoxazole and benzothiazole groups as raw materials, and adopts bromination and debromination methods to synthesize the corresponding heteroaryl acetylene compounds. Background technique: [0002] Heteroaryl acetylene compounds containing benzoxazole and benzothiazole groups refer to acetylene derivatives with two aryl groups, one of which is benzoxazolyl or benzothiazolyl, The other aromatic ring can be an aromatic or heteroaromatic ring such as phenyl, naphthyl, pyridyl, benzoxazolyl, benzothiazolyl, etc. Its typical structure is as follows: [0003] (1), phenylethynyl benzoxazole and phenylethynyl benzothiazole derivatives [0004] [0005] where X=O or S [0006] R=H, C1~C10 alkyl, C1~C10 alkoxy, F, Cl, Br, I, CN, etc. [0007] R'=H, C1~C10 alkyl, C1~C10 alkoxy, F, Cl, Br, I, CN, etc. [0008] (2), naphthynyl benzoxazole and naphthynyl benzothiazole derivatives [0009] [...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D263/32C07D277/22C07D277/24C07D277/28C07D401/06
Inventor 庄俊鹏姜龙张曙光郝海军
Owner BEIJING UNIV OF CHEM TECH
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