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Imidazo[2,1-b]benzothiazole compound and its synthesis method

A technology of benzothiazole and synthesis method, applied in the field of imidazo[2, can solve rare problems and the like, and achieve the effects of reducing reaction cost, high atom economy and stable molecular structure

Active Publication Date: 2019-07-02
XIANGTAN UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, currently there are few methods for synthesizing such substances

Method used

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  • Imidazo[2,1-b]benzothiazole compound and its synthesis method
  • Imidazo[2,1-b]benzothiazole compound and its synthesis method
  • Imidazo[2,1-b]benzothiazole compound and its synthesis method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 17

[0092] Example 1 Synthesis of 7,8,9,10-tetrahydrobenzo[4,5]imidazo[2,1-b]benzothiazole

[0093]

[0094] Take a reaction tube, add 0.025mmol (6.4mg) elemental sulfur (S 8 ), 0.2mmol (31mg) 2-aminobenzothiazole, 0.3mmol (31.2μL) cyclohexanone, 0.1mL DMSO, 0.5mL cyclohexane, reacted at 130°C for 24 hours, and conventionally processed to obtain 39.5mg of pure product, the product The rate is 86%.

Embodiment 1

[0095] The NMR and mass spectrometry data of embodiment 1 product are as follows:

[0096] 1 H NMR (400MHz, CDCl 3 , ppm) δ7.67-7.62 (m, 2H), 7.38 (t, J = 7.76Hz, 1H), 7.27 (t, J = 7.68Hz, 1H), 3.07-3.04 (m, 2H), 2.77-2.74 (m, 2H), 2.00-1.95(m, 2H), 1.92-1.86(m, 2H); 13 C NMR (100MHz, CDCl 3 , ppm) δ145.1, 142.4, 132.9, 129.7, 125.5, 123.9, 123.5, 121.8, 111.9, 24.8, 22.8, 22.7, 21.8; MS (EI) m / z (%) 228, 200 (100), 160, 108, 51; HRMScalcd.for: C 13 h 13 N 2 S + (M+H) + 229.07940, found 229.07941.

[0097] According to the operating method described in Example 1, the present invention has synthesized the following compounds:

[0098]

[0099]

[0100]

[0101]

[0102]

[0103] The pointer data such as nuclear magnetic field, mass spectrometry etc. of compound of the present invention are provided below:

Embodiment 2、3

[0104] Example 2,3 Synthesis of 9-methyl-7,8,9,10-tetrahydrobenzo[4,5]imidazo[2,1-b]benzothiazole

[0105]

[0106] 1 H NMR (400MHz, CDCl 3 , ppm) δ7.68-7.64 (m, 2H), 7.41-7.37 (m, 1H), 7.30-7.28 (m, 1H), 3.18 (dd, J=15.08, 5.4Hz, 1H), 2.80-2.76 ( m, 2H), 2.67-2.60(m, 1H), 2.13-2.05(m, 1H), 1.99-1.93(m, 1H), 1.62-1.52(m, 1H), 1.19(d, J=6.68Hz, 3H); 13 C NMR (100MHz, CDCl 3 , ppm) δ145.3, 142.2, 132.9, 129.8, 125.6, 124.0, 123.6, 121.7112.1, 31.2, 29.9, 29.4, 24.3, 21.4; MS (EI) m / z (%) 242, 200 (100), 160, 108, 51; HRMS calcd.for: C 14 h 15 N 2 S + (M+H) + 243.09505, found 243.09482.

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Abstract

The invention provides imidazo[2,1-b]benzothiazole compounds and a synthesis method thereof. According to the technical scheme, a metal catalyst is not needed, imidazo[2,1-b]benzothiazole and derivatives thereof are prepared from 2-benzothiazolamine compounds and ketone through conversion with air or oxygen as an oxidizing agent and one or a mixture of the following components as an organic solvent only under the action of elemental sulfur S8: cyclohexane, toluene, chlorobenzene, 1,2-dichlorobenzene, pyridine, quinoline, triethylamine, NMP, DMF, DMAc, DMSO, 1,4-dioxane and the like. The difficulty that the metal catalyst or a starting material with relatively higher activity is needed in the conventional synthesis method of the imidazo[2,1-b]benzothiazole compounds is overcome, and the compounds are suitable for preparing various functional materials, bioactive molecules and drug molecules.

Description

technical field [0001] The invention relates to an imidazo[2,1-b]benzothiazole compound and a synthesis method thereof. Background technique [0002] Imidazo[2,1-b]benzothiazole compounds are widely used and are important raw materials for the preparation of multifunctional materials, pesticides and medicines. However, there are not many methods for synthesizing such substances at present. For example Org.Biomol.Chem., 2012, 10, 7944; Chem.Heter ºCycl.Compd., 2013, 49, 345; Tetrahedron Lett., 2014, 55, 3367; Chem.Heter ºCycl.Compd., 2013, 49, 345; Org. Lett., 2014, 16, 6084; J. Org. Chem., 2015, 80, 9321 have reported some methods of synthesizing such substances. Most of these methods require the use of metal catalysts or relatively active starting materials. Contents of the invention [0003] In view of the above situation, the object of the present invention is to provide a kind of imidazo[2,1-b]benzothiazole and its derivatives, which have stable molecular structure ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D513/04
CPCC07D513/04
Inventor 邓国军谢艳军黄华文肖福红
Owner XIANGTAN UNIV
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