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Preparing method of 2-substituted-1,3-dithiane derivative

A technology of derivatives and dithianes, which is applied in the field of preparation of 2-substituted-1,3-dithiane derivatives, achieves the effects of high substrate conversion rate, simple and easy post-treatment, and high yield

Inactive Publication Date: 2018-09-14
LANZHOU UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

No reports have been found on the use of visible light activation to prepare 2-substituted-1,3-dithiane derivatives

Method used

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  • Preparing method of 2-substituted-1,3-dithiane derivative
  • Preparing method of 2-substituted-1,3-dithiane derivative
  • Preparing method of 2-substituted-1,3-dithiane derivative

Examples

Experimental program
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Effect test

Embodiment 1

[0021] The synthetic method of 2-phenyl substituted-1,3-dithiane comprises the following steps:

[0022] (1) Add 0.55mmol of 1,3-propanedithiol, 0.5mmol of benzaldehyde and 0.015mmol of Eosin Y to a 10mL colorless transparent glass test tube, add 1.5mL of MeCN to dissolve, and stir the system at room temperature 30°C , with a 3w blue LED light for 3h.

[0023] (2) After the reaction was completed, MeCN was removed by rotary evaporation under reduced pressure and the resulting mixture was separated by silica gel column chromatography to obtain the product.

[0024] The specific synthetic reaction formula is:

[0025]

[0026] After detection, the characterization result of the obtained 2-phenyl substituted-1,3-dithiane is: the yield is 98%, white solid. 1 H NMR (400MHz, CDCl 3 )δ7.53–7.41(m,2H),7.40–7.28(m,3H),5.17(s,1H),3.16–2.98(m,2H),3.00–2.83(m,2H),2.27–2.08( m,1H),2.05–1.82(m,1H); 13 C NMR (101MHz, CDCl 3 )δ 139.0, 128.7, 128.4, 127.7, 51.4, 32.1, 25.0.

Embodiment 2

[0028]

[0029] The product is as shown above, and the reaction conditions and steps are the same as in Example 1. After testing, the characterization result of the obtained product is: the yield is 99%, white solid. 1 H NMR (400MHz, CDCl3) δ7.33 (d, J = 8.0Hz, 2H), 7.13 (d, J = 8.0Hz, 2H), 5.13 (s, 1H), 3.05–2.98 (m, 2H), 2.88 –2.83(m,2H),2.31(s,3H),2.14–2.09(m,1H),1.86–1.82(m,1H); 13 C NMR (101 MHz, CDCl3) δ 138.1, 136.0, 129.2, 127.4, 51.0, 32.0, 24.9, 21.1.

Embodiment 3

[0031]

[0032] The product is as shown above, and the reaction conditions and steps are the same as in Example 1. After detection, the characterization result of the obtained product is: the yield is 74%, white solid. 1 H NMR (400MHz, CDCl3) δ7.47 (d, J = 8.4Hz, 2H), 7.35 (d, J = 8.4Hz, 2H), 5.11 (s, 1H), 3.15–2.97 (m, 2H), 2.93 –2.88(m,2H),2.20–2.14(m,1H),1.96–1.87(m,1H); 13 CNMR (101MHz, CDCl3) δ138.0, 131.9, 129.5, 122.3, 50.6, 31.9, 24.9.

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Abstract

The invention belongs to the technical field of organic synthesis, and particularly discloses a preparing method of a 2-substituted-1,3-dithiane derivative. The preparing method comprises the following steps of adding substrate aldehyde, 1,3-dimercaptopropane and catalytic amount Eosin Y into a proper amount of acetonitrile, continuously stirring the mixture, using a blue LED to irradiate the mixture for 3 h at a room-temperature open system, after the reaction is finished, removing organic solvents through rotary evaporation, and then obtaining a product through recrystallization and chromatography. According to the preparing method of the 2-substituted-1,3-dithiane derivative, the yield of the product is high, the conversion rate of the substrate is high, the reaction operation conditions are mild and environmentally friendly, demanding water and oxygen removal operations and devices are not needed, and the reaction can be conducted at the room temperature.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a preparation method of 2-substituted-1,3-dithiane derivatives. Background technique [0002] The 2-position monosubstituted 1,3-dithiane is widely used as a synthetic building block in the synthesis of natural products and drug molecules with good physiological activities. It is a preferred starting point for synthetic and medicinal chemists to construct carbonyl compounds. original thing. The traditional method for preparing dithiane is to use the activation of Lewis acid or protonic acid to dehydrate and condense the carbonyl of aldehyde or ketone compound with 1,3-propanedithiol. Because this traditional preparation method needs to add a large amount of acidic substances, and most of them need to be heated to reflux, the tolerance of the substrate is not good, and the post-reaction treatment and product purification are cumbersome, which restricts its w...

Claims

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Application Information

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IPC IPC(8): C07D339/08C07D409/04
CPCC07D339/08C07D409/04
Inventor 谢新刚邢志敏厍学功
Owner LANZHOU UNIVERSITY
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