Preparation method of 2-aryl benzoxazole and 2-aryl benzothiazole compounds

A technology of benzothiazole and benzoxazole, which is applied in the field of preparation of 2-aryl benzoxazole compounds, can solve complex processing problems and achieve the effect of reducing production costs

Active Publication Date: 2017-05-17
FUDAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The other is the condensation of 2-aminophenol (thiophenol) with benzyl alcohol, benzaldehyde, and benzoic acid, wherein the synthesis with benzyl alcohol requires the use of transition metals (see: ACS Catal. 2014, 4, 1686; Org. Lett. 2009, 11, 2039); while the use of benzoic acid requires the use of polyphosphoric acid and the disadvantages of complicated treatment (see: J. Heterocyclic Chem.2002, 39, 421)

Method used

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  • Preparation method of 2-aryl benzoxazole and 2-aryl benzothiazole compounds
  • Preparation method of 2-aryl benzoxazole and 2-aryl benzothiazole compounds
  • Preparation method of 2-aryl benzoxazole and 2-aryl benzothiazole compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0018] Example 1, 5-methyl-2-phenylbenzoxazole

[0019] Add 5mmol of 4-methyl-2-aminophenol 0.615g and 5 mmol of benzaldehyde 0.530g, 15ml of xylene into a 50ml reaction tube, stir at 120°C for 15 minutes, after the reaction is detected by TLC, add 1 mmol of imidazole Salt (4) 174mg, 1.25mmol potassium carbonate 175mg, reacted for 10 hours, the solution was spin-dried under reduced pressure, and then the obtained crude product was separated by column chromatography to obtain a product greater than 0.888 g, and the yield was greater than 85%.

[0020] Product structural formula (I)

[0021]

[0022] The characterization data are as follows:

[0023] 1 H NMR (400 MHz, CDCl 3 ) δ 8.24 (d, J = 3.6 Hz, 2H), 7.54 (d, J = 9.1 Hz,1H), 7.49 (s, 3H), 7.42 (d, J = 8.3 Hz, 1H), 7.12 (d, J = 8.2 Hz, 1H), 2.46(s, 3H); 13 C NMR (101 MHz, CDCl 3 ) δ 163.04, 148.96, 142.29, 134.30, 131.30,128.81, 127.50, 127.29, 126.17, 119.89, 109.89, 21.49. m / z (relative intensity, %...

Embodiment 2

[0024] Example 2, 2-(3-bromophenyl)-5-methyl-benzoxazole

[0025] Add 5mmol of 4-methyl-2-aminophenol 0.615g and 5 mmol of 3-bromobenzaldehyde 0.925g, 15ml of xylene into a 50ml reaction tube, stir at 120°C for 30 minutes, use TLC to detect the completion of the reaction, add 0.5mmol imidazolium salt (5) 109mg, 1.25mmol potassium carbonate 175mg, reacted for 15 hours, the solution was spin-dried under reduced pressure, and then the obtained crude product was separated by column chromatography to obtain a product greater than 1.31 g, and the yield was greater than 85%.

[0026] Product structure formula (II)

[0027]

[0028] The characterization data are as follows:

[0029] 1 H NMR (400 MHz, CDCl 3 ) δ 8.38 (t, J = 1.5 Hz, 1H), 8.15 (d, J = 7.8 Hz,1H), 7.63 (d, J = 8.0 Hz, 1H), 7.54 (s, 1H), 7.44 (d, J = 8.3 Hz, 1H), 7.37(t, J = 7.9 Hz, 1H), 7.17 (d, J = 8.3 Hz, 1H), 2.48 (s, 3H); 13 C NMR (101 MHz, CDCl 3 ) δ 161.48, 148.97, 142.05, 134.63, 134.19, 130.37...

Embodiment 3

[0030] Embodiment 3, 5-chloro-2-(methoxyphenyl)-benzoxazole

[0031]Add 5mmol of 4-chloro-2-aminophenol 0.615g and 5 mmol 2-methoxybenzaldehyde 0.680g, 15ml of xylene into a 50ml reaction tube, stir at 120°C for 10 minutes, and use TLC to detect the completion of the reaction. Add 109 mg of 0.5 mmol of imidazolium salt (5) and 175 mg of 1.25 mmol of potassium carbonate. After 12 hours of reaction, the solution is spin-dried under reduced pressure, and the obtained crude product is separated by column chromatography to obtain more than 1.10 g of the product, and the yield is more than 85%.

[0032] Product structure formula (III)

[0033]

[0034] The characterization data are as follows:

[0035] 1 H NMR (400 MHz, CDCl 3 ) δ 8.10 (d, J = 7.5 Hz, 1H), 7.78 (d, J = 1.0 Hz,1H), 7.52 – 7.45 (m, 2H), 7.28 (dd, J = 8.6, 1.5 Hz, 1H), 7.11 – 7.03 (m, 2H), 3.99 (s, 3H); 13 C NMR (101 MHz, CDCl 3 ) δ HRMS (ESI) Calcd for C 14 h 11 ClNO 2 : (M+H + ) 260.0478 (100.0%...

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Abstract

The invention belongs to the technical field of organic synthesis, and in particular relates to a preparation method of 2-aryl benzoxazole and 2-aryl benzothiazole compounds. According to the invention, 2-aminophenol(2-aminothiophenol) and aromatic aldehydes are stirred at the temperature of 100 to 130 DEG C, imidazolium salt of which the molar equivalent amount is 10% to 20% and K2CO3 of which the molar equivalent amount is 25% to 50% are added, air is used as an oxidant, and then 2-aryl benzoxazole and 2-aryl benzothiazole compounds are synthesized by a reaction. According to the invention, the cheap and easily prepared imidazolium salt is taken as a catalyst and the cheap air is taken as the oxidant to synthesize target products in a high yield, so that the preparation method of the 2-aryl benzoxazole and 2-aryl benzothiazole compounds is greatly lowered in production cost and capable of adapting to the industrial application to a greater extent.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a preparation method of 2-aryl benzoxazole (thiazole) compounds. Background technique [0002] Benzoxazole compounds widely exist in the fields of biology and medicine, have biological activities such as inhibiting bacteria, fungi, and parasites, and are an important class of heterocyclic molecular skeletons with aromatic properties (see: Eur. J. Med. Chem .2005, 40, 949; J. Heterocyclic Chem. 2011, 48, 1126; J. Med. Chem. 1993, 36,953; J. Med. Chem. 2013, 56, 4028), such as 2-arylbenzoxazole Such compounds have been used in research on the treatment of Alzheimer's disease (see: J. Med. Chem. 2012, 55, 9136; Chem. Soc. Rev. 2013, 42, 7747). In addition, due to the properties of 2-aryl benzox (thia) azole in fluorescence, it has been applied in the photosensitive catalyst of metal iridium, and has excellent catalytic performance for some specific reactions (...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D263/57C07D413/04C07D417/04C07D277/66
CPCC07D263/57C07D277/66C07D413/04C07D417/04
Inventor 侯秀峰周泉
Owner FUDAN UNIV
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