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A kind of polysubstituted furanocycloheptatriene pyrrole derivative and preparation method thereof

A technology of cycloheptatrienylpyrrole and multi-substituted furan, which is applied in the field of multi-substituted furocycloheptatrienylpyrrole derivatives and their preparation, can solve the problems of low atom utilization, complex process, and harsh reaction conditions, etc., and achieve 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: 2022-07-22
SHANDONG NORMAL UNIV
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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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  • A kind of polysubstituted furanocycloheptatriene pyrrole derivative and preparation method thereof
  • A kind of polysubstituted furanocycloheptatriene pyrrole derivative and preparation method thereof
  • A kind of polysubstituted furanocycloheptatriene pyrrole derivative and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

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

[0050]

[0051] To a 15mL pressure tube, add p-methoxyphenylisonitrile 1a (0.3mmol), 3-(3-phenylpropyl-2-yn-1-ylidene)-2,4-pentanedione 2a (0.75 mmol), and was dissolved in dichloromethane (2 mL), a stirring bar was added, zinc chloride (0.3 mmol) was added, and after stirring at room temperature for 10 minutes, m-chloroperoxybenzoic acid (0.3 mmol) was added to the reaction system, Continue to stir the reaction system at room temperature for 18h, at which time TLC monitors the complete formation of 3aa, then add aqueous sodium bisulfite solution (0.1N×5mL) to the system to quench the reaction, and then use dichloromethane (10mL×3) Extract the water phase, mix the obtained organic phases, add anhydrous sodium sulfate to dry, then evaporate the organic solvent by a rotary evaporator, and finally, separate by silica gel column chromatography to obtain the final product. Detection confirme...

Embodiment 2

[0055] Preparation of polysubstituted furanocycloheptatriene pyrrole derivatives 3ba:

[0056]

[0057] Using p-bromophenylisonitrile 1b instead of p-methoxyphenylisonitrile 1a in Example 1, other conditions were the same as in Example 1, to obtain a polysubstituted furanocycloheptatriene pyrrole derivative 3ba with a yield of 74% .

[0058] image 3 is the hydrogen nuclear magnetic spectrum of the furanocycloheptatriene pyrrole derivative obtained in Example 2 of the present invention, Figure 4 For its carbon NMR 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 calculated for C 35 H 26 ...

Embodiment 3

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

[0062]

[0063] Using p-ethoxycarbonyl phenyl isonitrile 1c instead of p-methoxyphenyl isonitrile 1a in Example 1, other conditions are the same as in Example 1, to obtain a polysubstituted furanocycloheptatriene pyrrole derivative 3ca with a yield of 72%.

[0064] Spectrogram 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 / zcalculated for C 38 H 31 NNaO 6 + ([M+Na] + ) 620.2044, found 620.2023.

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Abstract

The invention discloses a polysubstituted furanocycloheptatriene pyrrole derivative and a preparation method thereof. a kind of; R 1 Aryl; R 2 is an alkyl group; R 3 is an acyl group. The preparation method is as follows: using isonitrile compounds and conjugated enynone compounds under the condition jointly promoted by zinc chloride and m-chloroperoxybenzoic acid, a cycloaddition series reaction is carried out to directly generate furanocycloheptatriene pyrrole derivatives The preparation method has the advantages of simple and mild reaction conditions, a wide range of substrates and easy availability, high atom utilization, and simple operation.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis chemistry, and relates to a polysubstituted furanocycloheptatriene pyrrole derivative and a preparation method thereof. Background technique [0002] The disclosure of information in this Background section is only for enhancement of understanding of the general background of the invention and should not necessarily be taken as an acknowledgement or any form of suggestion that this information forms the prior art already known to a person of ordinary skill in the art. [0003] Pyrrolocycloheptane backbones are commonly found in natural product molecules. Pyrrolocycloheptane 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 inventor's research, some pyrrolocycloheptane derivatives have the effect of inhibiting the production of n...

Claims

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Application Information

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Patent Type & Authority Patents(China)
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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