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A method for synthesizing indole substituted or ferrocene substituted azaarenes

A technology of azaaromatics and ferrocene, applied in the field of chemical synthesis, can solve the problems of high cost, limited application, large pollution, etc., and achieve the effects of convenient separation, simple and practical operation, and high yield

Inactive Publication Date: 2020-03-10
QINGDAO AGRI UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, there are few methods for constructing azoarenes and indole or ferrocene skeletons at the same time. Moreover, the coupling reaction of benzylic C(sp3)-H bonds of azaarenes and alcohols usually requires the participation of precious metals, resulting in large pollution and high cost. high, making its application limited

Method used

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  • A method for synthesizing indole substituted or ferrocene substituted azaarenes
  • A method for synthesizing indole substituted or ferrocene substituted azaarenes
  • A method for synthesizing indole substituted or ferrocene substituted azaarenes

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0033] Embodiment 1: optimization of conditions

[0034] Take 0.2mmol of 2-methylquinoline compounds, 0.1mmol of indole alcohol or ferrocenol and 0.01mmol of TfOH in a sealed tube, add 2mL of solvent, stir at 120°C for reaction, and determine the reaction by TLC. After the reaction is completed, cool to room temperature, rotary evaporate, and chromatographic column separation.

[0035] Under the same reaction conditions, the solvents used are different, and the reaction yields are also different, and the specific yields are as follows:

[0036]

[0037]

[0038] Note: Yields are isolated yields.

Embodiment 2

[0039] Embodiment 2: the method that synthetic indole replaces or ferrocene replaces azaarene:

[0040]

Embodiment 3

[0042]

[0043] The product that present embodiment makes carries out nuclear magnetic resonance analysis:

[0044] Isolated yield: 93%, 1H NMR (500MHz, DMSO) δ11.06(s, 1H), 8.01(d, J=8.4Hz, 1H), 7.85(d, J=8.4Hz, 1H), 7.81(d, J =8.0Hz,1H),7.74(d,J=8.0Hz,1H),7.68(t,J=7.6Hz,1H),7.49(t,J=7.4Hz,1H),7.40-7.32(m,7H ),7.30(d,J=8.0Hz,1H),7.22(t,J=7.6Hz,2H),7.11(t,J=7.3Hz,1H),7.06(t,J=7.5Hz,1H), 7.02(d, J=8.4Hz, 1H), 6.97(t, J=7.5Hz, 1H), 5.25–5.19(m, 1H), 3.98–3.88(m, 2H).

[0045] 13C NMR (125MHz, DMSO) δ161.0, 147.3, 144.9, 136.3, 135.7, 135.5, 132.9, 129.3, 128.6, 128.4, 128.3, 128.2, 127.7, 127.6, 127.4, 127.0, 126.4, 125.1.7, 125 ,118.8,113.1,111.5,42.5,41.1.

[0046] HRMS(ESI):calcd.for C31H24N2[M+H]+:425.2018,found:425.2020

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Abstract

The present invention discloses a method for synthesizing indole-substituted or ferrocene substituted aza aromatic hydrocarbon, wherein the method can be performed in a solvent 1,4-dioxane at a temperature of 120 DEG C under the catalysis of TfOH. The invention provides the method for synthesizing the indole-substituted or ferrocene substituted aza aromatic hydrocarbon, wherein the proton acid-catalyzed dewatering coupling reaction between the benzyl site of the aza aromatic hydrocarbon and the indole alcohol or ferrocene alcohol is achieved, the method has characteristics of simple and easily-available raw materials, simple and practical operation, high reaction activity, complete raw material conversion, easy separation and high yield, and the reaction has characteristics of green economy and environmental protection.

Description

technical field [0001] The invention relates to the technical field of chemical synthesis, in particular to a method for synthesizing indole-substituted or ferrocene-substituted azaarenes. Background technique [0002] Indole and azaaromatic compounds are closely related to human life, and widely exist as "dominant skeletons" in natural products and drug molecules. The ferrocene framework is also widely used in organic catalysis. At present, there are few methods for constructing azoarenes and indole or ferrocene skeletons at the same time. Moreover, the coupling reaction of benzylic C(sp3)-H bonds of azaarenes and alcohols usually requires the participation of precious metals, resulting in large pollution and high cost. High, so its application is limited. [0003] [0004] references [0005] (a) Ackermann, L. Chem. Rev. 2011, 111, 1315. [0006] (b) Blank, B.; Kempe, R. J. Am. Chem. Soc. 2010, 132, 924. [0007] (c) Obora, Y.; Ogawa, S.; Yamamoto, N. J. Org. Chem....

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F17/02
CPCC07F17/02
Inventor 肖建朱帅王亮
Owner QINGDAO AGRI UNIV
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