A kind of method for preparing nitrogen-containing heterocyclic compound

A nitrogen heterocyclic compound and water content technology, applied in the direction of organic chemistry, etc., to achieve the effect of wide application, easy operation and good regioselectivity

Active Publication Date: 2021-07-02
GUANGDONG PHARMA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0007] But so far, no one has used it to prepare ketone compounds with heterocycles

Method used

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  • A kind of method for preparing nitrogen-containing heterocyclic compound
  • A kind of method for preparing nitrogen-containing heterocyclic compound
  • A kind of method for preparing nitrogen-containing heterocyclic compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Add 42.1mg (0.1mmol) of the enyne raw material shown below into a 4ml reaction flask with a stirring bar, add 2mL of wet dichloromethane (water content 1%) at room temperature, and then add 0.4uL (0.01mmol) of Tris Fluoromethanesulfonic acid was stirred at room temperature for 2 hours, spin-dried and separated by preparative thin-layer chromatography to obtain the target product with a yield of 66%.

[0029]

[0030] The detection results of the target product are as follows:

[0031] 1 H NMR (400MHz, CDCl 3 )δ7.85–7.80(m,2H),7.67(d,J=8.3Hz,2H),7.57–7.51(m,1H),7.44(dd,J=10.5,4.7Hz,2H),7.29(t ,J=6.7Hz,2H),3.72–3.65(m,2H),3.22(dd,J=4.7,2.0Hz,1H),3.11(dd,J=12.9,4.8Hz,1H),2.62–2.53( m,2H),2.43(s,3H),1.59–1.53(m,1H),1.47(dd,J=12.6,3.1Hz,1H),1.37(ddd,J=13.4,10.6,5.7Hz,2H) ,1.31–1.22(m,2H),1.11(s,3H),0.95(s,3H),0.81(s,3H).

[0032] 13 C NMR (101MHz, CDCl 3 )δ200.47,143.38,138.36,134.54,132.95,129.66,128.77,128.15,127.82,51.57,44.21,43.15,42.33,41.66,36.50,36.28,33.02...

Embodiment 2

[0035] Add 43.5mg (0.1mmol) of the enyne substrate shown below into a 4ml reaction flask with a stirring bar, add 2mL of wet dichloromethane (water content 1%) at room temperature, and then add 0.4uL (0.01mmol) Trifluoromethanesulfonic acid was stirred at room temperature for 2 hours, spin-dried and separated by preparative thin-layer chromatography to obtain the target product with a yield of 68%.

[0036]

[0037] The detection results of the target product are as follows:

[0038] 1 H NMR (400MHz, CDCl 3 )δ7.73(d, J=8.2Hz, 2H), 7.67(d, J=8.3Hz, 2H), 7.29(d, J=8.0Hz, 2H), 7.23(d, J=8.0Hz, 2H) ,3.71–3.60(m,2H),3.20(dd,J=4.7,2.1Hz,1H),3.11(dd,J=12.9,4.7Hz,1H),2.69–2.53(m,2H),2.42(s ,3H),2.40(s,3H),1.62–1.50(m,1H),1.45(dd,J=12.6,3.2Hz,1H),1.41–1.32(m,2H),1.30–1.20(m,2H ),1.11(s,3H),0.94(s,3H),0.80(s,3H).

[0039] 13 C NMR (101MHz, CDCl 3 )δ200.06,143.75,143.33,135.85,134.64,129.64,129.45,128.32,127.84,51.38,44.17,43.22,42.33,41.68,36.54,36.25,33.02,32.50,22.27,21.71,2...

Embodiment 3

[0042] Add 44.0mg (0.1mmol) of the enyne substrate shown below into a 4ml reaction flask with a stirring bar, add 2mL of wet dichloromethane (water content 1%) at room temperature, and then add 0.4uL (0.01mmol) Trifluoromethanesulfonic acid was stirred at room temperature for 2 hours, spin-dried and separated by preparative thin-layer chromatography to obtain the target product with a yield of 64%.

[0043]

[0044] 1 H NMR (400MHz, CDCl 3)δ7.86(ddd, J=8.3,5.2,2.5Hz,2H),7.67(d,J=8.2Hz,2H),7.30(d,J=7.9Hz,2H),7.16–7.06(m,2H ),3.70–3.60(m,2H),3.16(dd,J=4.6,1.9Hz,1H),3.12–3.05(m,1H),2.62–2.50(m,2H),2.43(s,3H), 1.64–1.56(m,2H),1.46–1.36(m,2H),1.30–1.21(m,2H),1.11(s,3H),0.95(s,3H),0.81(s,3H).

[0045] 13 C NMR (101MHz, CDCl 3 )δ198.80, 166.98, 164.33, 143.43, 134.65 (d, J = 17.4Hz), 130.79 (d, J = 9.2Hz), 129.68, 127.80, 115.85 (d, J = 21.8Hz), 51.60, 44.23, 43.19, 42.34 ,41.65,36.55,36.34,33.03,32.50,22.26,21.69,21.07,18.58.

[0046] 19 F NMR (377MHz, CDCl 3 )δ-105.69. ...

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Abstract

The invention belongs to the technical field of preparation of nitrogen-containing heterocyclic compounds, and in particular relates to a method for preparing nitrogen-containing heterocyclic compounds. It comprises the following steps: the method uses the raw materials shown in the following formula 1 or 2 to undergo an isomerization reaction under the catalysis of a protonic acid catalyst to prepare nitrogen-containing heterocyclic compounds of formula 3 or 4 respectively; the protonic acid catalyst For trifluoromethanesulfonic acid, trifluoromethanesulfonate ester, boron trifluoride-diethyl ether complex or bis(trifluoromethanesulfonyl)imide; the method provided by the invention can prepare monocyclic or polycyclic nitrogen-containing hetero Cyclic compounds, simple and easy to operate, no need for metal participation, wide range of reaction substrates, good regioselectivity, high yield, can quickly synthesize various types of nitrogen-containing heterocyclic compounds, and have broad applications in the preparation of natural products and drugs application prospects.

Description

technical field [0001] The invention belongs to the technical field of preparation of nitrogen-containing heterocyclic compounds, and in particular relates to a method for preparing nitrogen-containing heterocyclic compounds. Background technique [0002] Ketones with nitrogen-containing heterocycles are ubiquitous in natural products, drugs, and bioactive molecules. In recent years, a great deal of effort has been devoted to the synthesis of such nitrogen-containing heterocyclic compounds. Among them, the transition metal-catalyzed cyclization of enynes can rapidly construct carbon-carbon bonds and is widely used in the synthesis of functionalized cyclic compounds. In particular, metallic gold-catalyzed functionalization of alkenes has been extensively reported. Because metal gold catalysts can coordinate with alkynes to activate alkyne structural units, the active species can undergo addition reactions with various nucleophiles. [0003] However, these methods usually r...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D217/18C07D207/48
CPCC07D207/48C07D217/18
Inventor 曹华郭鹏峰余跃
Owner GUANGDONG PHARMA UNIV
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