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Polysubstituted furo-cycloheptatriene pyrrole derivative and preparation method thereof

A technology of cycloheptatriene pyrrole and polysubstituted furan, which is applied in the field of polysubstituted furanocycloheptatriene pyrrole derivatives and preparation thereof, can solve the problems of low atom utilization rate, complicated process, severe reaction conditions and the like, and achieves The raw materials and reagents are stable and easy to obtain, the preparation method is simple, and the water and oxygen tolerance is good.

Active Publication Date: 2021-05-28
SHANDONG NORMAL UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the inventors have found that most of the bioactive pyrrolopeptane derivative molecules are obtained from organisms by means of extraction and separation, and there are few reports on the chemical synthesis of the pyrrolopeptane skeleton.
The existing methods have problems such as complex process, serious waste of raw materials, cumbersome operation steps, harsh reaction conditions, and low utilization of atoms, and there are also certain technical difficulties in operation.

Method used

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  • Polysubstituted furo-cycloheptatriene pyrrole derivative and preparation method thereof
  • Polysubstituted furo-cycloheptatriene pyrrole derivative and preparation method thereof
  • Polysubstituted furo-cycloheptatriene pyrrole derivative and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] Preparation of polysubstituted furocycloheptatriene pyrrole derivatives 3aa:

[0050]

[0051] Add p-methoxyphenylisonitrile 1a (0.3mmol), 3-(3-phenylpropyl-2-yn-1-ylidene)-2,4-pentanedione 2a (0.75 mmol), and dissolve with dichloromethane (2mL), add stirring bar, add zinc chloride (0.3mmol), after stirring at room temperature for 10 minutes, add m-chloroperoxybenzoic acid (0.3mmol) in the reaction system, Continue to stir the reaction system at room temperature for 18 h. At this time, TLC monitors that 3aa is completely formed. Then, aqueous sodium bisulfite solution (0.1N×5 mL) is added to the system to quench the reaction, and dichloromethane (10 mL×3) Extract the aqueous phase, mix the obtained organic phases and add anhydrous sodium sulfate to dry, then evaporate the organic solvent through a rotary evaporator, and finally, separate the final product through silica gel column chromatography, and obtain the final product through nuclear magnetic hydrogen spectrum...

Embodiment 2

[0055] Preparation of multi-substituted furocycloheptatrienyl pyrrole derivatives 3ba:

[0056]

[0057] P-bromophenylisonitrile 1b was used to replace p-methoxyphenylisonitrile 1a in Example 1, and other conditions were the same as in Example 1 to obtain a multi-substituted furocycloheptatrienyl pyrrole derivative 3ba with a yield of 74% .

[0058] image 3 It is the nuclear magnetic hydrogen spectrogram of the furo cycloheptatrienyl pyrrole derivative obtained in Example 2 of the present invention, Figure 4 Its nuclear magnetic carbon spectrum, spectrum analysis data:

[0059] 1 H NMR (400MHz, CDCl 3 )δ7.44–7.39(m,4H),7.39–7.33(m,1H),7.22–7.16(m,3H),7.10(t,J=7.5Hz,2H),6.92–6.87(m,2H) ,6.60(d,J=8.6Hz,2H),2.58(s,3H),2.18(s,3H),1.98(s,3H),1.44(s,3H). 13 C NMR (101MHz, CDCl 3 )δ200.8,196.6,177.8,162.0,150.9,139.8,139.3,138.2,136.8,136.1,134.2,133.3,132.7,131.9,131.2,130.4,130.3,128.6,128.5,127.8,127.6,126.2,122.5,122.3,120.8 ,32.5,30.0,13.4,11.9.HRMS(ESI-TOF)m / z calc...

Embodiment 3

[0061] Preparation of polysubstituted furocycloheptatriene pyrrole derivatives 3ca:

[0062]

[0063] Use p-ethoxycarbonylphenyl isonitrile 1c to replace p-methoxyphenyl isonitrile 1a in Example 1, and other conditions are the same as in Example 1 to obtain multi-substituted furocycloheptatriene pyrrole derivatives 3ca with a yield of 72%.

[0064] Spectral analysis data:

[0065] 1 H NMR (400MHz, CDCl 3 )δ7.74(d,J=8.4Hz,2H),7.43–7.33(m,5H),7.12–7.06(m,1H),7.05–7.00(m,2H),6.94–6.88(m,2H) ,6.81(d,J=8.4Hz,2H),4.38(q,J=7.1Hz,2H),2.58(s,3H),2.18(s,3H),1.95(s,3H),1.44(s, 3H), 1.40(t, J=7.1Hz, 3H). 13 C NMR (101MHz, CDCl 3 )δ200.7,196.6,177.9,165.3,162.1,150.9,141.7,139.8,139.2,138.3,136.1,134.1,133.3,132.9,131.2,130.5,130.0,129.9,128.8,128.6,128.5,127.8,127.7,126.3,122.5 , 120.8, 61.3, 32.5, 30.0, 14.2, 13.4, 11.9. HRMS (ESI-TOF) m / z calculated for C 38 h 31 NNaO 6 + ([M+Na] + )620.2044, found 620.2023.

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Abstract

The invention discloses a polysubstituted furo-cycloheptatriene pyrrole derivative and a preparation method thereof, the structural general formula of the polysubstituted furo-cycloheptatriene pyrrole derivative is as shown in formula I, in the formula I, R is selected from one of aryl, fused aryl, alkyl or hydrogen atom; R1 is an aryl group; R2 is an alkyl group; and R3 is an acyl group. The preparation method comprises the following steps: carrying out cycloaddition cascade reaction on an isonitrile compound and a conjugated eneyne ketone compound under the condition of co-promotion of zinc chloride and m-chloroperoxybenzoic acid to directly generate the furo-cycloheptatriene pyrrole derivative. The preparation method has simple and mild reaction conditions, a wide range of substrates and easy availability, and the atom utilization rate is high; the operation is simple and convenient.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis chemistry, and relates to a multi-substituted furocycloheptatriene pyrrole derivative and a preparation method thereof. Background technique [0002] The information disclosed in this background section is only intended to increase the understanding of the general background of the present invention, and is not necessarily taken as an acknowledgment or any form of suggestion that the information constitutes the prior art already known to those skilled in the art. [0003] Pyrrolopeptane skeletons are commonly found in natural product molecules. Pyrrolopeptane derivatives have attracted the attention of researchers in the fields of chemistry, medicine and life sciences because of their unique structural characteristics and good biological activities. According to the research of the inventors, some pyrrolocycloheptane derivatives have the effect of inhibiting the production of nitric oxi...

Claims

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Application Information

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IPC IPC(8): C07D491/048
CPCC07D491/048
Inventor 徐显秀李朝阳王进胡忠燕白胜欣吴腾腾
Owner SHANDONG NORMAL UNIV
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