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Prrole derivative as well as synthetic method and application thereof

A synthetic method and derivative technology, applied in the direction of drug combination, organic chemistry, non-central analgesics, etc., can solve the problems of cumbersome synthesis of raw materials, high temperature requirement, limited substrate, etc., and achieve good yield, simple raw materials, The effect of easy access to raw materials

Inactive Publication Date: 2015-07-29
EAST CHINA NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the existing technologies have disadvantages such as high temperature requirement, cumbersome raw material synthesis, and limited substrates.

Method used

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  • Prrole derivative as well as synthetic method and application thereof
  • Prrole derivative as well as synthetic method and application thereof
  • Prrole derivative as well as synthetic method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Embodiment 1: Synthesis of 1-benzoyl-3-carboxylic acid ethyl ester-5-phenylpyrrole

[0036]

[0037] Acylamine-substituted enynyl esters, gold and silver catalysts, and solvents were selected from (E)-1-benzamido-2-(ethyl acetate)-4-phenylbutyne, AuPPh 3 Cl, AgNO 3 , toluene, the amount of raw material is o-bromoacetylenone 1-(2'-bromophenyl)-2-phenylethynyl ketone 0.2mmol, 5% AuPPh 3 Cl, 10% AgNO 3 , solvent 2ml, and reacted at 100° C. for 6 hours to obtain the target product formula (IA), a light yellow solid, and the separation yield was 97%. mp 154-156°C.

[0038] NMR data: 1 H NMR (400MHz, CDCl 3, Me 4Si) δ1.34(t, J=6.8Hz, 3H), 4.31(q, J=7.2Hz, 2H), 6.83(d, J=1.2Hz, 1H), 7.21-7.29(m, 5H), 7.42 (t, J=7.6Hz, 2H), 7.57(t, J=7.2Hz, 1H), 7.68(d, J=1.2Hz, 1H), 7.77(d, J=7.2Hz, 2H); 13 C NMR (100.6MHz, CDCl 3 , Me 4 Si) δ14.06, 60.26, 113.91, 118.79, 127.78, 128.27, 128.42, 128.77, 128.89, 130.80, 132.27, 132.55, 133.97, 137.32, 164.37, 168.79.

[0039] HRMS...

Embodiment 2

[0041] Embodiment 2: Synthesis of 1-benzoyl-3-carboxylic acid ethyl ester-5-(4'-methoxy)phenylpyrrole

[0042]

[0043] Acylamine-substituted enynyl esters, gold and silver catalysts, and solvents were selected from (E)-1-benzamido-2-(ethyl acetate)-4-(4'-methoxy)phenylbutyne, AuPPh 3 Cl, AgNO 3 , toluene, the amount of raw material is o-bromoacetylenone 1-(2'-bromophenyl)-2-phenylethynyl ketone 0.2mmol, 5% AuPPh 3 Cl, 10% AgNO 3 , solvent 2ml, and reacted at 100° C. for 6 hours to obtain the target product formula (IB), a light yellow solid, and the separation yield was 96%. mp 111-112°C.

[0044] NMR data: 1 H NMR (400Hz, CDCl 3 , Me 4 Si) δ1.25(t, J=7.2Hz, 3H), 3.68(s, 3H), 4.22(q, J=7.2Hz, 2H), 6.67(d, J=1.2Hz, 1H), 6.72(d ,J=8.8Hz,2H),7.13(d,J=8.8Hz,2H),7.35(t,J=8Hz,2H),7.50(t,J=7.6Hz,1H),7.55(d,J= 1.6Hz, 1H), 7.69(d, J=7.6Hz, 2H); 13 C NMR (100.6MHz, CDCl 3 , Me 4 Si)δ14.03,55.05,60.17,113.13,113.80,118.61,124.75,128.34,128.84,129.54,130.74,132.56,133.89,13...

Embodiment 3

[0046] Embodiment 3: Synthesis of 1-benzoyl-3-carboxylic acid ethyl ester-5-(4'-methyl)phenylpyrrole

[0047]

[0048] Acylamine-substituted enynyl esters, gold and silver catalysts, and solvents were selected from (E)-1-benzamido-2-(ethyl acetate)-4-(4'-methyl)phenylbutyne, AuPPh 3 Cl, AgNO 3 , toluene, the amount of raw material is o-bromoacetylenone 1-(2'-bromophenyl)-2-phenylethynyl ketone 0.2mmol, 5% AuPPh 3 Cl, 10% AgNO 3 , solvent 2ml, and reacted at 100° C. for 6 hours to obtain the target product formula (IC), a yellow solid, and the separation yield was 92%. mp 110-111°C.

[0049] NMR data: 1 H NMR (400MHz, CDCl 3 , Me 4 Si) δ1.25(t, J=7.2Hz, 3H), 2.22(s, 3H), 4.22(q, J=6.8Hz, 2H), 6.70(d, J=1.6Hz, 1H), 6.99(d ,J=7.6Hz,2H),7.10(d,J=8Hz,2H),7.36(t,J=8Hz,2H),7.50(t,J=7.6Hz,1H),7.56(d,J=1.2 Hz,1H),7.70(d,J=7.6Hz,2H); 13 C NMR (100.6MHz, CDCl 3 , Me 4 Si) δ14.02, 20.84, 60.17, 113.46, 118.66, 128.10, 128.54, 128.85, 129.10, 129.33, 130.76, 132.52, 133.89, 1...

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Abstract

The invention discloses a pyrrole derivative shown in the formula (I) (in the description) and a synthetic method thereof. Acyl amine substituted eneyne ester compounds are adopted as raw materials, and the pyrrole derivative shown in the formula (I) is obtained through synthesis under the action of a catalyst. The preparation method provided by the invention has the advantages that the raw materials are simple and easy to obtain, the universality is good, the post-processing is simple and convenient, the yield is high, and the environment friendliness is achieved. The invention further provides application of the pyrrole derivative shown in the formula (I) in preparation of pain-relieving and inflammation-diminishing drugs.

Description

technical field [0001] The invention belongs to the field of organic compound synthesis, and in particular relates to pyrrole derivatives co-catalyzed by gold and silver, and a synthesis method and application thereof. Background technique [0002] Pyrrole compounds are an important class of organic compounds, which are the main structural units in many natural products and medicines, and most of them have strong biological activities. It can be used as an intermediate in organic synthesis and has great value in drug synthesis. Therefore, much attention has been paid to the synthesis research of pyrrole compounds. At present, there are many reports on the synthesis methods of such compounds, and great progress has been made. For example, pyrrole derivatives can be obtained under the action of metals, alkalis, nitrogen carbenes and other salts. For example: literature (1) Chen, Z.; Lu, B.; Ding, Z.; Gao, K.; Yoshikai, N. Org. Lett.2013, 15, 1966. T.; Fu, S.; Li, X.; Deng,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D207/34A61P29/00
CPCC07D207/34
Inventor 李艳忠周园园孙霞郑重张芳芳陶相华
Owner EAST CHINA NORMAL UNIV
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