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A kind of synthetic method of 2-aminoquinolone compound

An aminoquinolone and a synthesis method technology, applied in the field of synthesis of 2-aminoquinolone compounds, can solve the problems of lack of synthesis method, lengthy steps, troublesome operation and the like, and achieve the effects of consistent reaction conditions, simple operation and high conversion rate

Active Publication Date: 2021-08-13
XI AN JIAOTONG UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

2-aminoquinolones have significant IMPDH inhibitory activity (WO2003035066A1, 2003), but their synthetic methods are relatively lacking. The synthetic methods of 2-aminoquinolones reported in the past have long steps, complex raw materials, cumbersome operations, and require high temperature conditions or Catalyst and other limitations (ChemistrySelect 2018,3,1176; Angew.Chem.,Int.Ed.2017,56,1805; J.Org.Chem.1999,64,3608; J.Chem.Soc.,Perkin Trans.1 1998, 2583)

Method used

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  • A kind of synthetic method of 2-aminoquinolone compound
  • A kind of synthetic method of 2-aminoquinolone compound
  • A kind of synthetic method of 2-aminoquinolone compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0061] Under nitrogen protection, 4-methylphenylisocyanate (0.5mmol) was added to ethoxyformylmethylenetriphenylphosphine (0.5mmol) in 1,2-dichloroethane (3mL) at 100°C Stir for 36-48 hours. After the reaction, cool to room temperature; concentrate by rotary evaporation, and perform column chromatography to obtain 124 mg of the product with a yield of 74%. The product is a yellow solid with a melting point of 222-224°C.

[0062] 1 H NMR (400MHz, DMSO-d 6 )δ10.69(br s,1H),10.60(br s,1H),7.80(s,1H),7.42(d,J=8.3Hz,1H),7.33(d,J=7.5Hz,1H), 7.28(m,4H),4.21(q,J=7.0Hz,2H),2.35(s,3H),2.34(s,3H),1.26(t,J=7.1Hz,3H).

[0063] 13 C NMR (100MHz, DMSO-d 6 )δ173.6, 169.6, 153.3, 135.2, 135.1, 134.3, 132.7, 132.0, 130.3, 124.9, 124.2, 123.9, 117.4, 93.3, 59.6, 20.6, 20.6, 14.3.

[0064] IRν max (neat):2956,1632,1578,1514,1434,1365,1281,1200,1148,1096,1018,807,742,665,556,541,520,489cm -1 .

[0065] HRMS (ESI) calcd for C 20 h 21 N 2 o 3 [M+H] + :337.1547,found:337.1540.

Embodiment 2

[0067] According to the method described in Example 1, the difference is that the substrates used are: 4-phenoxyphenyl isocyanate (0.5mmol), ethoxyformyl methylene triphenylphosphine (0.5mmol) and 1,2-bis Ethyl chloride (3mL) yielded 118mg of the product with a yield of 48%. The product was a yellow solid with a melting point of 157-159°C.

[0068] 1 H NMR (400MHz, DMSO-d 6 )δ10.82(br s,1H),10.59(br s,1H),7.58(d,J=8.9Hz,1H),7.43(ddd,J=16.3,7.1,2.7Hz,7H),7.31(dd ,J=8.9,2.8Hz,1H),7.18(t,J=7.4Hz,2H),7.11–7.03(m,6H),4.20(q,J=7.0Hz,2H),1.25(t,J= 7.1Hz, 4H).

[0069] 13 C NMR (100MHz, DMSO-d 6 )δ 172.9, 169.4, 156.6, 156.6, 154.7, 153.4, 152.7, 133.3, 132.2, 130.1, 130.1, 126.5, 125.2, 123.7, 123.6, 123.5, 119.8, 119.6, 118.8, 118.9, 93.7, 112

[0070] IRν max (neat):2977,1632,1582,1524,1503,1485,1368,1303,1280,1217,1161,1095,1051,872,844,807,768,742,706,688,566,523,506,428cm -1 .

[0071] HRMS (ESI) calcd for C 30 h 25 N 2 o 5 [M+H] + :493.1758,found:493.1762.

Embodiment 3

[0073] According to the method described in Example 1, the difference is that the substrates used are: 4-trifluoromethylphenylisocyanate (0.5mmol), ethoxyformylmethylenetriphenylphosphine (0.5mmol) and 1,2- Dichloroethane (3 mL) yielded 144 mg of the product with a yield of 65%. The product was a yellow solid with a melting point of 124-126°C.

[0074] 1 H NMR (400MHz, CDCl 3 )δ12.79(br s,1H),9.54(br s,1H),8.36(s,1H),7.92(d,J=8.5Hz,2H),7.76(dd,J=8.8,2.1Hz,1H ), 7.62(dd, J=18.9, 8.7Hz, 3H), 4.59(q, J=7.1Hz, 2H), 1.58(t, J=7.1Hz, 3H).

[0075] 13 C NMR (100MHz, CDCl 3 )δ169.8, 169.3, 152.6, 142.6, 129.0 (q, J = 10Hz), 128.2127.1, 126.1 (q, J = 12Hz), 124.2 (q, J = 289Hz), 125.1, 124.8, 122.9, 122.8, 121.9 (q, J=13Hz), 116.9, 93.6, 63.5, 14.1.

[0076] IRν max (neat):3392,1660,1635,1597,1547,1443,1415,1316,1257,1150,1110,1064,1011,950,908,870,850,834,730,609,525,414cm -1 .

[0077] HRMS (ESI) calcd for C 20 h 15 f 6 N 2 o 3 [M+H] + :445.0982,found:445.0974.

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Abstract

The invention discloses a method for synthesizing 2-aminoquinolones. The Wittig / rearrangement / 6π electrocyclization / isomerization series reaction occurs with phosphorus ylides and isocyanates under heating conditions to obtain 2-aminoquinolones compound. In the synthesis method disclosed in the present invention, one kind of isocyanate compound can be selected to react with phosphorus ylides to synthesize 2-aminoquinolones, or different isocyanates can be selected to react with phosphorus ylides step by step to synthesize 2-aminoquinolones. The synthesis method disclosed by the invention is simple to operate, easy to obtain raw materials, mild reaction conditions, no catalyst is needed, and the product is easy to separate and purify, which solves the technical difficulties of the synthesis method in the prior art with complicated steps and complicated raw materials, and is an improvement on the existing synthesis technology The breakthrough has high application value.

Description

technical field [0001] The invention belongs to the technical field of chemical synthesis, and in particular relates to a synthesis method of 2-aminoquinolone compounds. Background technique [0002] Quinolones have broad-spectrum antibacterial activity and are widely used as antibacterial drugs in clinical treatment, including the treatment of genitourinary tract infection, intestinal infection, respiratory tract infection, skeletal system infection, skin and soft tissue infection, etc. According to the different inventions and antibacterial properties, quinolone drugs are divided into first, second, third, and fourth generations. The fourth generation of quinolones has the largest antibacterial spectrum at present, and typical drugs include moxifloxacin and gatifloxacin. , Clinfloxacin et al. [0003] Because quinolones are widely used clinically, it is of great significance to develop efficient synthesis methods of quinolones. 2-Aminoquinolones have significant IMPDH in...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D215/56
CPCC07D215/56
Inventor 徐四龙张科强韩文丹卡基·拉文德拉·巴布李志
Owner XI AN JIAOTONG UNIV
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