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 skele

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

Example Embodiment

[0048]Example 1

[0049]Preparation of multi-substituted furan and cycloheptular triylpyrrole derivatives 3AA:

[0050]

[0051]Add to 15 ml of pressure tubes 1a (0.3 mmol), 3- (3-phenylpropylene-2-alkyne-1-subunit) -2,4-pentanone 2a (0.75) Mmol) and dissolved with dichloromethane (2 mL), adding a stirrer, adding zinc chloride (0.3 mmol), stirred at room temperature for 10 minutes, adding methyl chlorine peroxybenzoic acid (0.3 mmol) to the reaction system. The reaction system was continued for 18 h under room temperature conditions. At this time, the TLC monitors 3AA completely generated, and then the reaction was added to the system aqueous sodium hydrogen sulfite solution (0.1 N × 5 mL), then dichloromethane (10 ml × 3) After extracting the water phase, the resulting organic phase was mixed after mixing anhydrous sodium sulfate, and then evaporate the organic solvent by rotary evaporator. Finally, the final product was separated by silica gel column chromatography. Magnetic spectrum, carb...

Example Embodiment

[0054]Example 2

[0055]Preparation of multi-substituted furan and cycloheptular triylpyrrole derivative 3ba:

[0056]

[0057]The pair of methoxybenzyl azimbonitrile 1a in Example 1 was used to give the bromine phenyl nitrile 1b, and the other conditions were as in Example 1, and the mixed furan and cycloheptular triylpyrrole derivative 3ba were obtained. The yield was 74%. .

[0058]image 3 For the nuclear magnetic hydrogen spectrum of furan and cycloheptular triylpyrrole derivatives obtained in Example 2 of the present invention,Figure 4For its nuclear magnetic carbon spectrum, spectrum analysis data:

[0059]1H NMR (400MHz, CDCL3Δ7.44-7.39 (m, 4H), 7.39-7.33 (m, 1H), 7.22-7.16 (m, 3H), 7.10 (t, j = 7.5 Hz, 2H), 6.92-6.87 (m, 2H) 6.60 (D, J = 8.6 Hz, 2H), 2.58 (S, 3H), 2.44 (S, 3H), 1.44 (S, 3H), 1.44 (S, 3H), 1.98 (S, 3H), 1.44 (S, 3H).13C NMR (101MHz, CDCL3) 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...

Example Embodiment

[0060]Example 3

[0061]Preparation of multi-substituted furan and cycloheptular triylpyrrole derivatives 3ca:

[0062]

[0063]The pair of methoxyphenyl nitrile 1a in Example 1 was used in this example, and the other conditions were used as in Example 1, and the yield was obtained by the same example in Example 1. 72%.

[0064]Spectral parsing data:

[0065]1H NMR (400MHz, CDCL3Δ7.74 (D, J = 8.4 Hz, 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 = 8.4 Hz, 2H), 4.38 (Q, J = 7.1 Hz, 2H), 2.58 (S, 3H), 2.44 (S, 3H), 1.44 (S, 3H), 1.40 (T, J = 7.1 Hz, 3H).13C NMR (101MHz, CDCL3) 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 / ZCALCULATED FOR C38Hide31Nnao6+([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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