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Preparation method of thiocyano-containing thiazoline compound

A technology of thiocyanothiazoline and thiocyanothiazoline, which is applied in the field of preparation of thiocyanothiazoline compounds, can solve the problems of long reaction time and cumbersome operation, and achieve short reaction time, simple operation and mild reaction conditions Effect

Active Publication Date: 2020-04-28
QINGDAO UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] Utilize above-mentioned method to synthesize thiazoline compound, have obvious shortcoming and deficiency: 1) needs heating; 2) operation is loaded down with trivial details; 3) reaction time is long

Method used

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  • Preparation method of thiocyano-containing thiazoline compound
  • Preparation method of thiocyano-containing thiazoline compound
  • Preparation method of thiocyano-containing thiazoline compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0021] Preparation of thiocyanothiazoline compound 3a

[0022]

[0023] Add N-allylbenzothioamide 1a (0.2mmol, 36mg), ammonium thiocyanate 2 (0.4mmol, 30mg) and acetonitrile (4mL) into a 10mL three-necked flask. Two graphite rods (Φ5mm) were used as anode and cathode respectively. The reaction mixture was stirred at room temperature for 5 hours at a constant voltage of 2V. After the reaction was complete, the solvent was removed using a rotary evaporator. The product 3a was obtained by silica gel flash chromatography using petroleum ether and ethyl acetate as eluents in 84% yield.

[0024] Spectral analysis data 3a:

[0025] 1 H NMR (CDCl 3 ,500MHz): δ7.85–7.78(m,2H),7.46(m,3H),4.64(dd,J=16.4,2.2,1H),4.41(dd,J=16.5,7.8,1H),4.27– 4.18(m,1H),3.16(dd,J=13.4,6.5,1H),3.05(dd,J=13.4,8.2,1H). 13 C NMR (CDCl 3 ,125MHz):δ166.8,132.6,131.7,128.7,128.4,111.3,68.5,50.1,38.9.HRMS(ESI-TOF,[M+H + ]): calcd for C 11 h 11 N 2 S 2 ,235.0364,found235.0369.

Embodiment 2

[0027] Replace 1a in Example 1 with 1b, and other conditions are the same as Example 1. The experimental results are shown in Table 1.

[0028]

[0029] Spectrum analysis data 3b:

[0030] 1 H NMR (CDCl 3 ,500MHz): δ7.79–7.59(m,2H),7.23(d,J=7.9,2H),4.62(dd,J=16.4,2.1,1H),4.39(dd,J=16.4,7.8,1H ),4.20(m,1H),3.15(dd,J=13.4,6.5,1H),3.04(dd,J=13.4,8.2,1H),2.40(s,3H). 13 C NMR (CDCl 3 ,125MHz):δ166.7,142.2,129.9,129.4,128.4,111.4,68.4,49.9,38.9,21.5.HRMS(ESI-TOF,[M+H + ]): calcd for C 12 h 13 N 2 S 2 ,249.0520,found 249.0524.

Embodiment 3

[0032] Replace 1a in Example 1 with 1c, other conditions are the same as Example 1, and the experimental results are shown in Table 1.

[0033]

[0034] Spectrum analysis data 3c:

[0035] 1 H NMR (CDCl 3 ,500MHz):δ7.80–7.74(m,2H),6.96–6.90(m,2H),4.60(dd,J=16.3,2.1,1H),4.37(dd,J=16.2,7.7,1H), 4.20(m,1H),3.85(s,3H),3.16(dd,J=13.4,6.5,1H),3.04(dd,J=13.4,8.2,1H). 13 C NMR (CDCl 3 ,125MHz):δ166.0,162.3,130.1,125.3,114.0,111.3,68.3,55.4,50.1.HRMS(ESI-TOF,[M+H + ]): calcd for C 12 h 13 N 2 OS 2 ,265.0469,found 265.0475.

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Abstract

The invention discloses a preparation method of a thiocyano-containing thiazoline compound, and belongs to the technical field of organic synthesis. The method comprises the following steps: adding thioamide, ammonium thiocyanate and a solvent into a reactor, performing reacting under the action of electrification, and after the reaction is finished, performing separating by silica gel column chromatography to obtain a pure target product. The preparation method of the thiocyano-containing thiazoline compound provided by the invention has the characteristics of scientificity, reasonability, mild conditions, simplicity in operation, short reaction time and the like. The reaction equation is shown in the specification.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a preparation method of sulfur-containing cyanothiazoline compounds. Background technique [0002] As an important class of heterocyclic compounds, thiazoline compounds have a wide range of physiological activities. Studies have shown that such heterocyclic compounds can be used as glutathione reductase inhibitors (Mol.Pharmaceutics 2018, 15, 3069), Has antitumor activity (J.Org.Chem.1961, 26, 3867) and antimitotic agent (Chem.Rev.2009, 109, 1371). At the same time, thiocyanate is a class of important compounds containing thiocyano functional groups, which have various biological activities, such as insecticidal (J.Med.Chem.2002, 45, 3984), antimicrobial (Pharm.Chem.J. 2013,47,422), etc., have important application value in the fields of medicine and pesticides. Therefore, it is of great significance to develop a new method for the green and efficient synth...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D277/10C07D417/04
CPCC07D277/10C07D417/04
Inventor 郭维斯张延安文丽荣李明
Owner QINGDAO UNIV OF SCI & TECH
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