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Polysubstituted difuro-cycloheptatrienamine derivative and preparation method thereof

A technology of cycloheptatrienylamine and difuran, which is applied in the field of multi-substituted bisfuranotropenylamine derivatives and its preparation, can solve the problems of waste of raw materials, many reaction steps, and low utilization rate of atoms

Inactive Publication Date: 2021-05-11
SHANDONG NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the inventors have found that most of the furanocycloheptane derivatives with good biological activity are obtained by extraction and separation from living organisms, and there are few reports on the chemical synthesis method of the furanocycloheptane skeleton.
The existing extraction and separation methods have problems such as cumbersome operation steps, complicated process, and serious waste of raw materials. At the same time, the chemical synthesis method also has problems such as harsh reaction conditions, many reaction steps, and low atom utilization. There are certain technical difficulties

Method used

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  • Polysubstituted difuro-cycloheptatrienamine derivative and preparation method thereof
  • Polysubstituted difuro-cycloheptatrienamine derivative and preparation method thereof
  • Polysubstituted difuro-cycloheptatrienamine derivative and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] Preparation of multi-substituted bisfurocyclohexatriene amine derivatives 3aa:

[0050]

[0051] Add p-methoxyphenylisonitrile 1a (0.3 mmol), 3-(3-phenylpropyl-2-yn-1-ylidene)-2,4-pentanedione 2a (0.6 mmol), and dissolved with dichloromethane (2mL), add a stirring bar, add zinc chloride (0.3mmol), tighten the pressure tube cock and put it into a metal module preheated to 90°C for stirring, the reaction time is 1.5h, At this time, TLC monitored the complete formation of 3aa, stopped the reaction and left it to room temperature, evaporated the solvent under reduced pressure, and separated by silica gel column chromatography to obtain the final product, which was confirmed to be multi-substituted by H NMR, C and mass spectrometry Bisfurocycloheptatriene amine derivative 3aa, the yield is 74%.

[0052] figure 1 It is the NMR spectrum of the bisfurocycloheptatrienylamine derivative obtained in Example 1 of the present invention, figure 2 Its nuclear magnetic carbon sp...

Embodiment 2

[0055] Preparation of multi-substituted bisfuro cycloheptatriene amine derivatives 3ba:

[0056]

[0057] Use p-bromophenylisonitrile 1b to replace p-methoxyphenylisonitrile 1a in Example 1, and other conditions are the same as in Example 1 to obtain multiple substituted bisfurocycloheptatrienylamine derivatives 3ba with a yield of 65 %.

[0058] image 3 It is the nuclear magnetic hydrogen spectrogram of the bisfurocycloheptatrienylamine 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 )δ7.38(t, J=7.2Hz, 2H), 7.33–7.28(m, 3H), 7.27–7.23(m, 3H), 7.22–7.17(m, 2H), 6.86(d, J=8.8Hz ,2H),6.42(s,1H),5.78(d,J=8.8Hz,2H),5.71(s,1H),2.55(s,3H),2.46(s,3H),2.40(s,3H) ,2.21(s,3H). 13 C NMR (101MHz, CDCl 3 )δ196.1,194.5,159.0,153.8,153.6,148.6,142.5,139.2,135.7,131.4,129.9,129.3,128.8,128.3,127.7,127.0,123.9,121.8,120.6,119.4,118.5,114.8,112.5,37.9,31.0 ,30.5,16.0,...

Embodiment 3

[0061] Preparation of multi-substituted bisfurocyclohexatriene amine derivatives 3ca:

[0062]

[0063] Use p-ethoxycarbonylphenylisonitrile 1c to replace p-methoxyphenylisonitrile 1a in Example 1, and other conditions are the same as in Example 1 to obtain multi-substituted bisfurocycloheptatrienylamine derivatives 3ca, yield 60%.

[0064] Spectral analysis data:

[0065] 1 H NMR (400MHz, CDCl 3 )δ7.44(d,J=8.8Hz,2H),7.35–7.28(m,4H),7.28–7.23(m,4H),7.22–7.17(m,2H),6.44(s,1H),6.25 (s,1H),5.85(d,J=8.8Hz,2H),4.24(q,J=7.1Hz,2H),2.56(s,3H),2.48(s,3H),2.46(s,3H) ,2.18(s,3H),1.31(t,J=7.1Hz,3H). 13 CNMR (101MHz, CDCl 3 )δ195.9,194.5,166.6,159.3,154.5,153.9,148.5,147.6,139.3,135.8,130.5,129.8,128.5,128.3,128.1,127.7,127.1,127.0,123.8,121.8,121.6,121.3,120.6,115.3,115.1 ,60.2,37.9,31.0,30.5,16.0,14.4,14.3.HRMS(ESI-TOF)m / zcalculated for C 38 h 33 NNaO 6 +

[0066] ([M+Na] + )622.2200, found 622.2196.

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Abstract

The invention discloses a polysubstituted difuro-cycloheptatrienamine derivative and a preparation method thereof. The structural general formula of the polysubstituted difuro-cycloheptatrienamine derivative is as shown in formula I, in the formula I, R is selected from one of aryl, fused aryl and alkyl, R1 is selected from one of aryl and fused aryl, R2 is selected from alkyl, R3 is shown in the specification, and R4 is selected from one of alkyl and alkoxy. The preparation method comprises the following steps: taking an isonitrile compound and a conjugated eneyne ketone compound as raw materials, and carrying out cycloaddition cascade reaction under the promotion condition of zinc chloride to directly generate the furo-cycloheptatriene derivative. The preparation method has the advantages of simple and mild reaction conditions, wide and easily available raw material range, high atom utilization rate, simplicity and convenience in operation and the like.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis chemistry, and relates to a multi-substituted bisfurocycloheptatrienylamine 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] Furocycloheptane derivatives have attracted extensive attention from 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 furocycloheptane derivatives have cardioprotective activity, and some furocycloheptane derivatives have neuroprotective effect, etc. However, the inventors hav...

Claims

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Application Information

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IPC IPC(8): C07D493/04
CPCC07D493/04
Inventor 胡忠燕李朝阳董金环李巧真魏倩雯周庆花
Owner SHANDONG NORMAL UNIV
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