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4,5-disubstituted-2-aminothiazole compound and its preparation method

A technology for aminothiazoles and compounds, applied in the field of compound synthesis, can solve problems such as poor applicability of different functional groups, difficulty in obtaining raw materials, and low product yields, and achieve the effects of low environmental pollution, high yields, and high yields

Inactive Publication Date: 2016-02-24
ZHEJIANG UNIV
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  • Abstract
  • Description
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AI Technical Summary

Problems solved by technology

[0009] Although there are many reports on the synthesis of 2-aminothiazole, the known synthesis methods still have problems such as difficult acquisition of raw materials, low product yield, poor applicability to different functional groups, and cumbersome operations.
In addition, the above method usually introduces an alkyl group, aryl group, hydrogen or alkoxy group at the 4-position of the thiazole ring, and there are few reports on the introduction of an acyl group or alkoxycarbonyl group at the 4-position of the thiazole ring.
[0010] The known method of introducing an acyl or alkoxycarbonyl group at the 4-position of the thiazole ring is usually to change the substrate α-halogenated ketone of the Hantzsch thiazole synthesis method into a 3-halogenated-1,2-propanedione compound, thereby in The 4th position of the thiazole ring introduces an acyl group (Raihan, MustafaJ. etal. Advanced Synthesis & Catalysis, 2012, 354, 2251), or the α-halogenated ketone is changed to a 3-halo-2-oxo-propionate compound in the thiazole ring 4 The introduction of alkoxycarbonyl (Roppe, JeffreyR; etal.WO2007117778), but the raw materials required for synthesis are difficult to obtain, and the reaction needs to be carried out under high temperature reflux conditions

Method used

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  • 4,5-disubstituted-2-aminothiazole compound and its preparation method
  • 4,5-disubstituted-2-aminothiazole compound and its preparation method
  • 4,5-disubstituted-2-aminothiazole compound and its preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] Embodiment 1, 4-(4-chlorobenzoyl)-5-phenyl-2-aminothiazole (m1)

[0050] Add 141.9 mg (0.5 mmol) of 1-p-chlorophenyl-2-azido-3-phenyl-2-propen-1-one and 97.2 mg (1 mmol) of potassium thiocyanate to the reaction flask, and then add CH 3 CH 2 CH 2 OH (n-propanol) 2.0ml, ferrous sulfate heptahydrate 69.5mg (0.25mmol), after the addition, stirred at 80°C for 12 hours, and TLC detected the reaction (petroleum ether: ethyl acetate = 1:1 volume ratio) .

[0051] Remarks: When TLC detection shows that 1-p-chlorophenyl-2-azido-3-phenyl-2-propen-1-one disappears, it means that the reaction has ended.

[0052] After the reaction was finished, concentrate to remove n-propanol, cool to room temperature, add 60ml of water, and extract the reaction solution three times with 3×20mL ethyl acetate, and wash the organic layer (at the upper layer) three times with 3×30mL saturated brine, and then use Anhydrous sodium sulfate (2.0g) was dried for 30 minutes, and concentrated by a rotar...

Embodiment 2

[0077] Embodiment 2, 4-benzoyl-5-phenyl-2-aminothiazole (m2)

[0078] Replace 1-p-chlorophenyl-2-azido-3-phenyl-2-propen-1-one with 1-phenyl-2-azido-3-phenyl-2-propen-1-one, mol Quantity is constant, all the other are equal to embodiment 1. 128.8 mg of the product 4-benzoyl-5-phenyl-2-aminothiazole was obtained as a yellow solid, with a yield of 92%.

[0079] Its structural formula is:

[0080]

[0081] Yellowsolid; mp:160.4-160.8℃; 1 HNMR (500MHz, DMSO) δ7.84 (d, J = 7.05, 2H), 7.59 (t, J = 6.88, 1H), 7.47 (d, J = 7.31, 2H), 7.35-7.24 (m, 7H); 13 CNMR (125MHz, DMSO) δ190.76, 166.14, 143.60, 137.12, 133.12, 131.11, 129.66, 128.99, 128.56, 128.39, 128.35, 127.59; HRMS (ESI): m / zcalcdforC 16 h 12 N 2 OS[M+H] + :281.0749,found:281.0748.

Embodiment 3

[0082] Example 3, 4-(4-methylbenzoyl)-5-phenyl-2-aminothiazole (m3)

[0083] Replace 1-p-chlorophenyl-2-azido-3-phenyl-2-propene-1-one with 1-p-methylphenyl-2-azido-3-phenyl-2-propene-1-one Ketone, molar weight is constant, all the other are equal to embodiment 1. 138.2 mg of the product 4-(4-methylbenzoyl)-5-phenyl-2-aminothiazole was obtained as a yellow solid, with a yield of 94%.

[0084] Its structural formula is:

[0085]

[0086] Yellowsolid; mp:189.4-189.9℃; 1 HNMR (500MHz, DMSO) δ7.75 (d, J=8.07, 2H), 7.33 (s, 2H), 7.28-7.21 (m, 7H), 2.35 (s, 3H); 13CNMR (125MHz, DMSO) δ190.63, 166.21, 143.88, 143.74, 134.45, 131.18, 129.85, 128.98, 128.60, 128.19, 127.91, 127.47, 21.22; HRMS (ESI): m / zcalcdforC 17 h 14 N 2 OS[M+H] + :295.0905,found:295.0907.

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Abstract

The invention discloses a 4, 5-disubstituted-2-aminothiazole compound. The structural formula is shown in the specification, wherein R1 is 4-tolyl, 4-chlorophenyl, 4-methoxyphenyl, 4-nitrobenzene or propoxy, and R2 is phenyl, 4-tolyl, 4-fluorophenyl, 4-methoxyphenyl, 2-furyl, isopropyl, 4-nitrophenyl or n-propyl. The invention simultaneously provides a preparation method of the 4, 5-disubstituted-2-aminothiazole compound. The preparation method comprises the following steps: enabling an olefin azide type compound and potassium thiocyanate to react at the temperature of 75-85 DEG C in the presence of a solvent and a metal catalyst, concentrating an obtained reaction solution, then extracting with water and ethyl acetate, washing an obtained organic layer, then drying and concentrating by a rotary evaporator; performing silica gel column chromatography on an obtained concentrate to obtain the 4, 5-disubstituted-2-aminothiazole compound.

Description

technical field [0001] The invention belongs to a synthesis method of a compound, and mainly relates to a 4,5-disubstituted-2-aminothiazole compound and a preparation method thereof. Background technique [0002] Thiazole compounds are an important class of heterocyclic compounds, which have important applications in the fields of medicine, agriculture, materials, and life sciences. Aminothiazole compounds can undergo a series of reactions through the amino functional group, and the compounds thus synthesized have a wide range of applications in pesticides, dyes, etc., such as for the synthesis of herbicides, monoazo disperse dyes, etc. 2-aminothiazole compounds are widely used in the synthesis of drugs for the treatment of tumors, hypertension and other diseases. [0003] Because of the important application value of 2-aminothiazole compound, its synthesis method has been widely concerned, and the most classic one is the thiazole synthesis method proposed by Hantzsch et al...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D277/40C07D417/04C07D277/56A61P35/00
CPCC07D277/40C07D277/56C07D417/04
Inventor 章国林陈斌辉倪航程俞永平
Owner ZHEJIANG UNIV
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