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Preparation method of benzodithiocyclopentadiene derivative

A technology for benzodithiocyclopentadiene and derivatives, which is applied in the field of preparation of benzodithiocyclopentadiene derivatives, can solve the problems of narrow substrate range, harsh reaction conditions, lack of practical value and the like, and achieves Easy separation and purification, rich synthesis methods, and green and environmentally friendly reaction systems

Active Publication Date: 2019-03-22
XUZHOU NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, these disclosed catalytic systems usually use thiophenol or its derivatives with pungent smell as "sulfur source", and they also generally have many shortcomings such as narrow substrate scope, harsh reaction conditions, low product yield, etc., which lack practicality. value

Method used

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  • Preparation method of benzodithiocyclopentadiene derivative
  • Preparation method of benzodithiocyclopentadiene derivative
  • Preparation method of benzodithiocyclopentadiene derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Example 1: Preparation of benzodithiocyclopentadiene derivative 2a, the experimental results are shown in Table 1.

[0030]

[0031] To a 50 mL Shrek bottle with a magnetic stirring device was added toluene (10 mL), N-phenyl-2-bromothiobenzamide 1a (0.291 g, 1.0 mmol) and S 8 (0.036g, 1.2mmol), add cuprous iodide (0.019g, 0.1mmol), 1,10-phenanthroline (0.036g, 0.2mmol), cesium carbonate (0.326g, 1.0mmol) after stirring, will It was placed in a 100°C oil bath and continued to stir. TLC detects that the substrate disappears, and the reaction ends. The reaction solution was poured into saturated aqueous sodium chloride solution (10mL), extracted with dichloromethane (3×10mL), and the organic phases were combined, then backwashed with water (3×10mL), dried over anhydrous calcium chloride, Steps such as suction filter, vacuum distillation obtain viscous solid, finally through silica gel column chromatography (eluent is V 石油醚 :V 乙酸乙酯 =20:1) A yellow solid was obtained,...

Embodiment 2

[0035] Replace 1a in Example 1 with 1b, wherein the amount of each material is: 1b (0.306g, 1.0mmol) and S 8 (0.036g, 1.5mmol), add cuprous iodide (0.19g, 1mmol), 1,10-phenanthroline (0.108g, 0.6mmol), cesium carbonate (0.65g, 2.0mmol); The non-aqueous solvent Select DMF (10 mL).

[0036] Other conditions are the same as Example 1, and the experimental results are shown in Table 1.

[0037]

[0038] Spectrum analysis data 2b:

[0039] Yellow solid, m.p.164-165℃; 1 H-NMR (400MHz, CDCl 3 )δ8.15(d,J=8.8Hz,1H),7.47-7.42(m,2H),7.32-7.28(m,1H),7.21(d,J=8.0Hz,2H),7.05(d,J =7.2Hz, 2H), 2.35(s, 2H); 13 C-NMR (CDCl 3,100MHz)δ164.8,147.9,144.2,133.8,131.7,130.7,129.2,125.7,124.4,122.3,118.8,20.0; HRMS(APCI)m / z calculated for C 14 h 11 NS 2 [M+H] + :258.0406found:258.0411.

Embodiment 3

[0041] Replace 1a in Example 1 with 1c, wherein the amount of each material is: 1c (0.312g, 1.0mmol) and S 8 (0.072g, 3mmol), add cuprous iodide (0.19g, 1mmol), 1,10-phenanthroline (0.18g, 1mmol), cesium carbonate (0.65g, 2.0mmol); Described non-aqueous solvent selects DMF (10 mL).

[0042] Other conditions are the same as Example 1, and the experimental results are shown in Table 1.

[0043]

[0044] Spectral analysis data 2c:

[0045] Yellow solid, m.p.173-174℃; 1 H-NMR (400MHz, CDCl 3 )δ8.18-8.15(m,1H),7.52-7.47(m,2H),7.37-7.33(m,1H),7.16-7.12(m,2H),6.99-6.95(m,2H),3.84( s,3H); 13 C-NMR (CDCl 3 ,100MHz)δ165.6,157.1,145.1,144.7,132.9,131.7,126.8,125.5,123.4,121.4,114.8,55.5; HRMS(APCI)m / z calculated for C 14 h 11 NOS 2 [M+H] + :274.0355found:274.0381.

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Abstract

The invention discloses a preparation method of a benzodithiocyclopentadiene derivative. Benzodithiocyclopentadiene is synthesized by reacting S8 as a sulfur source with 2-bromothioamide. The synthesis method provides a cheap, easily available and environment-friendly synthesis method for synthesis of benzodithiocyclopentadiene compounds, adopts a green and environment-friendly reaction system, obtains products easy to be separated and purified, is suitable for synthesizing various highly functionalized benzodithiocyclopentadiene compounds, is particularly suitable for large-scale industrial production, and can prepare high-purity benzodithiocyclopentadiene compounds at high efficiency and high yield.

Description

technical field [0001] The invention belongs to organic synthesis chemistry technology, in particular to a preparation method of benzodithiocyclopentadiene derivatives. Background technique [0002] Benzodithiocyclopentadiene (BDT) is a class of molecules with good biological activity, often showing strong anti-hepatitis B virus (J Labeled Compd Rad.2012,55,197), anti-mycobacterium tuberculosis (Bioorg Med ChemLett.2008,18,3706) and anti-diarrheal activity (J.Med.Chem.2004,47,5265). At the same time, as an important intermediate of fine chemical products, benzodithiocyclopentadiene has a wide range of uses in the fields of food, pesticides, daily chemicals, coatings, textiles, printing and dyeing, papermaking, photosensitive materials, and polymer materials. However, only a very small amount of benzodithiocyclopentadiene compounds can be isolated from natural substances, and the cost is expensive. Therefore, the artificial synthesis of these substances is therefore of part...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D339/04C07D495/04
CPCC07D339/04C07D495/04
Inventor 吕兰兰黄梦乔刘建全王香善
Owner XUZHOU NORMAL UNIVERSITY
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