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Green synthesis method of 3-phenanthridinyl propyl formate compound

A technology for phenanthridine propyl formate and green synthesis, which is applied in the field of synthesis of phenanthridine and its derivatives, can solve the problems of not being universally applicable, difficult to obtain reaction raw materials, harsh reaction conditions, etc., to avoid catalysts and additives The effect of easy use, easy product and mild reaction conditions

Active Publication Date: 2019-10-11
HUAIBEI NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, in these methods, there are still certain limitations: such as the need to add catalysts and oxidants, the reaction raw materials are not easy to obtain, the reaction conditions are harsh, there are many steps, the yield is not high, and it is not universally applicable, etc.
And there is no synthetic report for 3-phenanthridine propyl carboxylate compound

Method used

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  • Green synthesis method of 3-phenanthridinyl propyl formate compound
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  • Green synthesis method of 3-phenanthridinyl propyl formate compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Such as figure 1 A green synthetic method of a shown 3-phenanthridine propyl carboxylate compound, the method may further comprise the steps:

[0033] (1) Accurately weigh 2-biphenylisonitrile (1a, 44.5 mg), and then add it into a reaction tube containing 2.0 mL of tetrahydrofuran and water (10:1);

[0034] (2) Place the reaction tube in step (1) on a 3W 380 nm LED lamp, and irradiate the reaction for 30 hours at room temperature. Under light irradiation, tetrahydrofuran selectively breaks the carbon-carbon bond;

[0035] (3) After the reaction, pour the reaction mixture into a separatory funnel filled with 10.0 mL of deionized water, extract and wash with ethyl acetate three times, 5.0 mL each time, and combine the organic phases;

[0036] (4) drying the organic phase obtained in step (3) with magnesium sulfate, suction filtration, removing magnesium sulfate, and concentrating the organic phase with a rotary evaporator to obtain a residue;

[0037] (5) The residue wa...

Embodiment 2

[0041] The difference from the preparation method in Example 1 is that the reaction raw material 1a is changed to 1b (2-isocyano-5-methyl-1,1'biphenyl, 48.3 mg), and other conditions are the same as in Example 1.

[0042] Column chromatography (silica gel, mobile phase: petroleum ether / ethyl acetate (9:1)) gave the target product 3b (48.9 mg, yield: 70%) as a colorless solid.

[0043] Such as Figure 4 , 5 As shown, compound 3b is characterized as follows: 1 H NMR (400 MHz, CDCl 3 ) δ: 8.58 (d, J =8.0 Hz, 1H), 8.28 (s, 1H), 8.17 (d, J = 8.0Hz, 1H), 8.11 (s, 1H), 7.98 (d, J = 8.4 Hz, 1H), 7.78 (td, J = 8.0, 1.2 Hz,1H), 7.64 (td, J = 8.0, 0.8 Hz, 1H),7.51 (dd, J = 8.4, 1.6 Hz, 1H), 4.38 (t, J = 6.4 Hz, 2H), 3.41 (t, J= 7.6Hz, 2H), 2.59 (s, 3H), 2.38-2.31 (m, 2H); 13 C NMR (100 MHz, CDCl 3 ) δ: 161.1, 159.1, 141.9, 136.2, 132.6, 130.2, 130.1, 129.3, 127.1, 125.6, 125.1, 123.4, 122.4, 121.5, 63.8, 31.7, 27.3, 21.8. HRMS (ESI) ([M+H] + ) calculated for C 18 H17NO 2 ...

Embodiment 3

[0045] The difference from the preparation method in Example 1 is that the reaction raw material 1a is changed to 1c (2-isocyano-5-chloro-1,1’biphenyl, 53.3 mg), and other conditions are the same as in Example 1.

[0046] Column chromatography (silica gel, mobile phase: petroleum ether / ethyl acetate (9:1)) gave the target product 3c (53.8 mg, yield: 72%) as a colorless solid.

[0047] Such as Figure 6 , 7 As shown, compound 3c is characterized as follows: 1 H NMR (400 MHz, CDCl 3 ) δ: 8.44 (d, J =8.0 Hz, 1H), 8.38 (s, 1H), 8.16 (d, J = 8.0 Hz, 1H), 8.12 (s, 1H), 7.97 (d, J = 8.4 Hz, 1H), 7.79 (t, J = 7.2 Hz, 1H), 7.68 (t, J = 7.6 Hz, 1H), 7.60 (d, J = 8.8 Hz, 1H), 4.39 (t, J = 6.0 Hz, 2H), 3.39 (t, J = 7.6 Hz, 2H), 2.38-2.31(m, 2H); 13 C NMR (100 MHz, CDCl 3 ( + ) calculated for C 17 H15ClNO 2 : 300.0786, found: 300.0788.

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Abstract

The invention discloses a green synthesis method of a 3-phenanthridinyl propyl formate compound. 2-biaryl isonitrile is accurately weighed and added into a reaction tube containing a mixed solution oftetrahydrofuran and water; the reaction tube is placed on a W 380nm LED lamp for irradiation reaction for some time at the room temperature; after the reaction is over, a reaction mixture is poured into a separating funnel containing deionized water, ethyl acetate is used for extraction and washing three times, and organic phases are combined; the obtained organic phases are dried with magnesiumsulfate, magnesium sulfate is removed through suction filtration, and the organic phases are condensed by using a rotary evaporator to obtain residues; the residues are subjected to column chromatography separation, and a target product 3-phenanthridinyl propyl formate compound is obtained. A simple and green light promotion strategy is adopted, a water containing system is used as a reaction solvent without adding a photocatalyst and an oxidant, and the 3-phenanthridinyl propyl formate compound is synthesized. The method has the advantages that the operation is simple, the raw materials are cheap and easy to obtain, the reaction condition is mild, the product is easy to separation, and the compatibility of the functional groups is excellent.

Description

technical field [0001] The invention relates to a synthesis method of phenanthridine and derivatives thereof, in particular to a green synthesis method of 3-phenanthridine propyl carboxylate compounds. Background technique [0002] Phenanthridine and its derivatives are a very important class of heterocyclic compounds, which have antibacterial, antitumor and other biological activities and photoelectric properties. Their structural units are widely found in some natural products, drugs and functional material molecules. In recent years, the synthesis of phenanthridine and its derivatives has received more and more attention from chemists. Therefore, exploring efficient and selective synthesis methods of phenanthridine compounds is of great significance in the fields of medicinal chemistry and materials science. Recently, the synthesis of phenanthridine derivatives via radical addition to 2-biarylisocyanide to generate imine radicals and intramolecular cyclization has been r...

Claims

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Application Information

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IPC IPC(8): C07D221/12
CPCC07D221/12
Inventor 苗涛石伟
Owner HUAIBEI NORMAL UNIVERSITY
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