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2-thio-1, 3, 4-thiadiazole-3-yl compound and preparation method thereof

A technology for thiadiazoles and compounds, which is applied in the field of preparing 2-thio-1, and can solve the problems that the structure has not been studied.

Inactive Publication Date: 2011-05-18
DALIAN UNIV OF TECH
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Problems solved by technology

[0004] In 2009, Marie Savonnet et al. did research on different secondary amines as nucleophiles for Michael addition reaction [J.Green Chemistry (11): 1729-1732], but the secondary amines they selected were limited to alkanes with side chains or cycloalkanes, structures where the N atom itself is inside the aromatic ring have not been studied

Method used

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  • 2-thio-1, 3, 4-thiadiazole-3-yl compound and preparation method thereof
  • 2-thio-1, 3, 4-thiadiazole-3-yl compound and preparation method thereof
  • 2-thio-1, 3, 4-thiadiazole-3-yl compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 15

[0030] Example 15-amino-2-mercapto-1,3,4-thiadiazole and acrylonitrile carry out Michael addition reaction

[0031] Dissolve 0.66g (5mmol) of 5-amino-2-mercapto-1,3,4-thiadiazole and 0.53g (10mmol) of acrylonitrile in 50ml of acetone, and keep it in a water bath at 30°C for 10h. The reaction system uses N 2 protection, the reaction solution gradually changed from colorless to dark reddish brown, and the acetone was evaporated under reduced pressure to obtain a dark brown viscous liquid. The product was purified by column chromatography and purified with ethyl acetate / cyclohexane (v / v=2:1 ) as developing agent; product yield 56.74%, melting point 103-105°C; pale yellow solid. Its reaction equation is route 4:

[0032]

[0033] Route 4

[0034] Test data: 1 H NMR (400MHz, Acteone) δ (ppm): 3.04 (t, J = 6.8Hz, 2H), 4.41 (t, J = 6.8Hz, 2H), 6.68 (s, 2H); IR (KBr) (v max , cm -1 ): 3415.573284.942173.661619.961553.681182.781066.83; the structure is determined to be 3-(5-ami...

Embodiment 25

[0035] Example 25-amino-2-mercapto-1,3,4-thiadiazole and methyl acrylate carry out Michael addition reaction

[0036] Dissolve 0.66g (5mmol) of 5-amino-2-mercapto-1,3,4-thiadiazole and 0.86g (10mmol) of methyl acrylate in 50ml of acetone, and keep it in a water bath at 30°C for 10h. The color gradually becomes light yellow, and the acetone is evaporated under reduced pressure to obtain a yellow viscous liquid, and the product is purified by column chromatography, using ethyl acetate / cyclohexane (v / v=2:1) ​​as a developing solvent; the product yield It is 49.36%, melting point is 119~121℃; light yellow solid. Its reaction equation is route 5:

[0037]

[0038] Route 5

[0039] Test data: 1H NMR (400MHz, Acteone) δ (ppm): 2.82(t, J=7.2Hz, 2H), 3.64(s, 3H), 4.36(t, J=4.8Hz, 2H), 6.60(s, 2H); IR(KBr)(v max , cm -1 ): 3416.453285.392924.551718.521620.161556.021213.291068.84; the structure is determined to be 3-(5-amino-2-thio-1,3,4-thiadiazol-3(2H)-yl)propionic acid methyl...

Embodiment 35

[0040] Example 35-amino-2-mercapto-1,3,4-thiadiazole and butyl acrylate carry out Michael addition reaction

[0041] Dissolve 0.66g (5mmol) of 5-amino-2-mercapto-1,3,4-thiadiazole and 1.28g (10mmol) of butyl acrylate in 50ml of acetone, keep it in a water bath at 30°C for 10h, and the reaction solution changes from colorless to Gradually turn pale yellow, acetone is evaporated under reduced pressure to obtain a yellow viscous liquid, the product is purified by column chromatography, using ethyl acetate / cyclohexane (v / v=2:1) ​​as a developing solvent; the product yield is 37.16%, light yellow viscous liquid at room temperature. Its reaction equation is route 6:

[0042]

[0043] Route 6

[0044] Test data: 1 H NMR (400MHz, Acteone) δ (ppm): 0.92(t, 3H), 1.41(m, J=8.0Hz, 2H), 1.61(m, J=8.0Hz, 2H), 2.83(t, J=8.0 Hz, 2H), 4.07(t, J=4.0Hz, 2H), 4.37(t, J=8.0Hz, 2H), 6.55(s, 2H); IR(KBr)(v max , cm-1): 3315.263191.402959.311724.151559.001256.081184.241068.83; the structure i...

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Abstract

The invention relates to a 2-thio-1, 3, 4-thiadiazole-3-yl compound and a preparation method thereof, which belong to the technical field of organic synthesis technology. The invention is characterized in that 3-N on five-membered aromatic heterocycle of 5-substitute-2-mercapto-1, 3, 4-thiadiazole and a double bond-contained alpha, beta-unsaturated compound perform Michael addition reaction underthe condition of alkaline catalysis to prepare the 2-thio-1, 3, 4-thiadiazole-3-yl compound on basis of the tautomeric characteristic of a molecular structure of the 5-substitute-2-mercapto-1, 3, 4-thiadiazole. The 2-thio-1, 3, 4-thiadiazole-3-yl compound and the preparation method thereof have the advantages that: different functional groups can be introduced into the 3-N of the 5-substitute-2-mercapto-1, 3, 4-thiadiazole as required to successfully synthesize the 2-thio-1, 3, 4-thiadiazole-3-yl compound.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and relates to the Michael addition reaction of 5-substituted-2-mercapto-1,3,4-thiadiazole with α,β-unsaturated compounds containing double bonds at its 3-N to obtain Preparation of 2-thio-1,3,4-thiadiazol-3-yls. Background technique [0002] 1,3,4-Thiadiazoles are an important part of azole heterocyclic compounds. As early as 50 years ago, it was discovered that 1,3,4-thiadiazole compounds have antibacterial and anti-inflammatory drug activity, and the antibacterial drug acetazolamide was synthesized. In recent years, 1,3,4-thiadiazole compounds have gradually been applied in the fields of industry, agriculture, and medicine, and breakthroughs have been made. For example: 1,3,4-thiadiazole compounds are applied to oil products as a new anti-wear and anti-extrusion agent for lubricating grease, which overcomes the shortcomings of traditional additives such as reduced oil resistance to...

Claims

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Application Information

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IPC IPC(8): C07D285/135
Inventor 陈宏博宋勇李文有
Owner DALIAN UNIV OF TECH
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