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3,5-Disubstituted-4-aminothiophene-2-carbaldehyde compound and preparation method thereof

An aminothiophene and compound technology, applied in the field of compound synthesis, can solve problems such as difficulty in obtaining raw materials, and achieve the effects of high yield and mild reaction temperature

Inactive Publication Date: 2015-11-18
ZHEJIANG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] Literature (Schatz, J.ScienceofSynthesis, 2002, 9, 287-422) reports the simultaneous introduction of two active groups of aldehyde group and amino group on the thiophene ring to synthesize the method of 3-aminothiophene-2-carbaldehyde compounds (formula 2), Raw materials used in this method are not readily available

Method used

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  • 3,5-Disubstituted-4-aminothiophene-2-carbaldehyde compound and preparation method thereof
  • 3,5-Disubstituted-4-aminothiophene-2-carbaldehyde compound and preparation method thereof
  • 3,5-Disubstituted-4-aminothiophene-2-carbaldehyde compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0058] Example 1, 4-amino-3-(4-chlorophenyl)-5-phenylthiophene-2-carbaldehyde (m1)

[0059] 141.9 mg (0.5 mmol) of 1-p-chlorophenyl-2-azido-3-phenyl-2-propen-1-one, 76.1 mg (0.5 mmol) of 1,4-dithio-2,5-diol ), added to the reaction flask, and then added 2.0ml of DMF (N,N-dimethylformamide), 207.3mg (1.5mmol) of potassium carbonate, after the addition was completed, the reaction was stirred at 40°C, and the reaction was detected by TLC (petroleum ether: Ethyl acetate = 6:1 volume ratio); the reaction was complete after 4 hours. After the reaction, the reaction solution was extracted three times with 3×20mL ethyl acetate, and the organic layer (located on the upper layer) was combined and washed three times with 3×30mL saturated brine, then dried with anhydrous sodium sulfate (2.0g) for 30 minutes, and rotary evaporated After being concentrated to near dryness, the gained concentrate is subjected to column chromatography (petroleum ether: ethyl acetate=8:1 volume ratio), and th...

Embodiment 2

[0078] Example 2, 4-amino-3-(4-nitrophenyl)-5-phenylthiophene-2-carbaldehyde (m2)

[0079] Replace 1-p-chlorophenyl-2-azido-3-phenyl-2-propene-1-one with 1-p-nitrophenyl-2-azido-3-phenyl-2-propene-1-one Ketone, molar weight is constant, all the other are with embodiment 1. 132.9 mg of the red solid product 4-amino-3-(4-nitrophenyl)-5-phenylthiophene-2-carbaldehyde was obtained, with a yield of 82%.

[0080] Its structural formula is:

[0081]

[0082] Redsolid; mp: 123.6–124.8℃; 1 HNMR (500MHz, CDCl 3 )δ9.61(s,1H),8.41(d,J=8.62Hz,2H),7.73(d,J=8.69Hz,2H),7.62(d,J=7.25Hz,2H),7.51(t, J=7.53Hz, 2H), 7.41(t, J=7.44, 1H), 3.78(s, 2H); 13 CNMR (125MHz, CDCl 3 )δ182.50, 148.03, 140.09, 139.09, 138.38, 137.05, 132.69, 131.15, 129.52, 128.63, 128.13, 127.20, 124.29; HRMS (ESI): m / zcalcdforC 17 h 12 N 2 o 3 S[M+H] + :325.0647,found:325.0645.

Embodiment 3

[0083] Example 3, 4-amino-3-(4-methylphenyl)-5-phenylthiophene-2-carbaldehyde (m3)

[0084] 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 with embodiment 1. 114.3 mg of the product 4-amino-3-(4-methylphenyl)-5-phenylthiophene-2-carbaldehyde was obtained as a yellow solid, with a yield of 78%.

[0085] Its structural formula is:

[0086]

[0087] Yellowsolid; mp:125.7–126.5℃; 1 HNMR (500MHz, CDCl 3 )δ9.61(s,1H),7.63(d,J=7.15Hz,2H),7.46(t,J=7.51Hz,2H),7.38–7.32(m,5H),3.79(s,2H), 2.44(s,3H); 13 CNMR (125MHz, CDCl 3 )δ184.01, 142.41, 140.43, 139.09, 136.41, 133.43, 129.94, 129.82, 129.33, 129.25, 128.14, 128.01, 125.86, 21.36; HRMS (ESI): m / zcalcdforC 18 h 15 NOS[M+H] + :294.0953,found:294.0949.

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Abstract

The invention discloses a 3,5-bisubstituted-4-aminothiophene-2-formaldehyde compound. The structural formula of the compound is shown in the description; wherein in the structural formula, the R1 represents C1, NO2, CH3, H or OCH3; and the R2 represents a phenyl group, a p-methoxyphenyl group, an m-bromophenyl group, a p-bromophenyl group, a 2-furyl group, or a p-methylphenyl group. The invention also discloses a preparation method of the compound. The prepared 3,5-bisubstituted-4-aminothiophene-2-formaldehyde compound can inhibit the tumor cell activity in vitro, and can be used as an anti-tumor lead compound.

Description

technical field [0001] The invention belongs to a synthesis method of a compound, and mainly relates to a 3,5-disubstituted-4-aminothiophene-2-carbaldehyde compound and a preparation method thereof. Background technique [0002] Thiophene compounds are an important class of heterocyclic compounds, mainly used in the synthesis of medicines, but also in the synthesis of dyes, resins, pesticides, spices, etc. Among them, thiophenecarbaldehyde is used to introduce thiophene groups into organic compounds, and is widely used in the pharmaceutical industry. For example, thiopheneethylamine, which is prepared by condensation and reduction of 2-thiophenecarbaldehyde and nitromethane, is the main ingredient of ticlopyridine hydrochloride, a drug for treating cardiovascular diseases. Raw materials; 2-thiophene carboxaldehyde is also used in the synthesis of anti-tumor drugs such as teniposide. [0003] Generally, an aldehyde group is introduced into thiophene by Vilsmeier reaction, su...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D333/36C07D409/04
CPCC07D333/36C07D409/04
Inventor 章国林陈斌辉倪航程俞永平
Owner ZHEJIANG UNIV