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Method for catalyzing conversion of carbonyl sulfide by using organic catalyst to synthesize five-membered sulfur heterocyclic compound

An organic catalyst and carbonyl sulfide technology, which is applied in the field of organocatalyst-catalyzed conversion of carbonyl sulfide to synthesize five-membered sulfur heterocyclic compounds, can solve the problems of poor applicability of reaction substrates and low reaction activity, and achieve simple and easy-to-obtain reaction raw materials and reagents, The post-processing process is simple and the operation is safe and simple.

Inactive Publication Date: 2018-06-15
DALIAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] Although the research work on building sulfur heterocyclic compounds with carbonyl sulfide as a sulfur source has been reported (D'Amico, JJ.; Fuhrhop, R.W.; Bollinger, F.G.; Dahl, W.E., J Heterocyclic Chem 1986,23,641-645.), but Most of the reaction system adopts stoichiometric reaction, and there are disadvantages such as poor applicability of reaction substrates and low reactivity.

Method used

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  • Method for catalyzing conversion of carbonyl sulfide by using organic catalyst to synthesize five-membered sulfur heterocyclic compound
  • Method for catalyzing conversion of carbonyl sulfide by using organic catalyst to synthesize five-membered sulfur heterocyclic compound
  • Method for catalyzing conversion of carbonyl sulfide by using organic catalyst to synthesize five-membered sulfur heterocyclic compound

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Experimental program
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Embodiment 1

[0032] In a 20 milliliter autoclave, add a stirring bar, 5.0 millimoles of 2-methyl-4-benzene-3-butyn-2-alcohol, 0.025 millimoles of THPE-COS (n=1, R 13 benzyl), after stirring at 60 degrees Celsius for 1 hour, stop heating and stirring, cool to room temperature, and slowly release unreacted carbonyl sulfide. The reaction solution in the reaction kettle was dissolved in 2 ml of dichloromethane and transferred to a 50-ml round-bottom single-necked flask, and the reaction kettle was rinsed with (3×2 ml) of dichloromethane, and then the crude product was obtained after removing the solvent in vacuo . The crude product was separated and purified by column chromatography (developing solvent: dichloromethane). The yield was 95%.

Embodiment 2

[0034] In 20 milliliter autoclave, add stirring bar, 5.0 millimoles of 2-methyl-3-butyn-2-alcohol, 0.025 millimoles of THPE-COS (n=1, R 13 benzyl), after stirring at 60 degrees Celsius for 1 hour, stop heating and stirring, cool to room temperature, and slowly release unreacted carbonyl sulfide. The reaction solution in the reaction kettle was dissolved in 2 ml of dichloromethane and transferred to a 50-ml round-bottom single-necked flask, and the reaction kettle was rinsed with (3×2 ml) of dichloromethane, and then the crude product was obtained after removing the solvent in vacuo . The crude product was separated and purified by column chromatography (developing solvent: dichloromethane). The yield was 92%.

Embodiment 3

[0036] In a 20 milliliter autoclave, add a stirring bar, 5.0 millimoles of 2-phenyl-3-butyn-2-alcohol, 0.025 millimoles of THPE-COS (n=1, R 13 For methyl), after stirring at 50 degrees Celsius for 2 hours, stop heating and stirring, cool to room temperature, and slowly release unreacted carbonyl sulfide. The reaction solution in the reaction kettle was dissolved in 2 ml of dichloromethane and transferred to a 50-ml round-bottom single-necked flask, and the reaction kettle was rinsed with (3×2 ml) of dichloromethane, and then the crude product was obtained after removing the solvent in vacuo . The crude product was separated and purified by column chromatography (developing solvent: dichloromethane). The yield was 93%.

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Abstract

The invention relates to a method for catalyzing the conversion of carbonyl sulfide by using an organic catalyst to synthesize a five-membered sulfur heterocyclic compound and belongs to the technicalfields of organic synthesis, pesticides as well as medicinal and chemical synthesis. The method comprises the steps: adding a propargyl derivative and a solvent into a high-pressure kettle; then, adding an organic catalyst; introducing carbonyl sulfide gas; carrying out stirring under the condition of 25-60 DEG C for 1-24h; after the reaction is ended, carrying out cooling to the room temperature, slowly releasing unreacted carbonyl sulfide gas, and draining the solvent to obtain a crude product; and carrying out purification to obtain 4-alkylenecyclic thiocarbonate, 5-alkylene-1,3-thiazolidane-2-ketone and 5-alkylene-1,3-thiazolidane-2,4-diketone compounds. In the method, a traditional sulfur source is replaced with carbonyl sulfide, the reaction has the characteristics of cleanness, mild reaction condition, high functional group tolerance, high conversion rate and stereoselectivity, and therefore, the method is widely applied to organic synthesis, pesticides and medicines.

Description

technical field [0001] The present invention relates to a method for synthesizing five-membered sulfur heterocyclic compounds by catalyzing the conversion of carbonyl sulfide by an organic catalyst, in particular to an organic catalyst catalyzing the cyclization of carbonyl sulfide and propargyl derivatives (propargyl alcohol, propargyl amine and propargyl amide) Synthesis of 4-alkylene cyclothiocarbonate, 5-alkylene-1,3-thiazolidin-2-one and 5-alkylene-1,3-thiazolidine-2,4-dione by reaction The compound method belongs to the technical field of organic synthesis, pesticide and pharmaceutical chemical synthesis. Background technique [0002] Five-membered sulfur-containing heterocyclic compounds are an important class of organic molecules, which can be used as drugs, insecticides, herbicides and medicines. Among them, thiazophosphine (S-sec-butyl-O-ethyl-2-oxo-1,3-thiazolidin-3-ylthiophosphonate) is a class of five-membered sulfur-containing heterocycles widely used at prese...

Claims

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Application Information

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IPC IPC(8): C07D327/04C07D277/34
CPCC07D277/34C07D327/04
Inventor 周辉张瑞吕小兵
Owner DALIAN UNIV OF TECH
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