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Synthesis method for constructing phenanthridine compound through ring opening cyclization of alkenyl benzotriazole under visible light catalysis

A technology of alkenyl benzotriazole and synthesis method, applied in the direction of organic chemistry and the like, can solve the problems of high substrate toxicity and poor substrate stability of phenanthrene

Pending Publication Date: 2022-08-09
HENAN UNIVERSITY
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Problems solved by technology

[0005] In order to solve the problems of poor substrate stability and high substrate toxicity in the existing synthesis of phenanthridine, the present invention provides a new method for constructing phenanthridine compounds by ring-opening and cyclization of alkenyl benzotriazole under visible light catalysis

Method used

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  • Synthesis method for constructing phenanthridine compound through ring opening cyclization of alkenyl benzotriazole under visible light catalysis
  • Synthesis method for constructing phenanthridine compound through ring opening cyclization of alkenyl benzotriazole under visible light catalysis
  • Synthesis method for constructing phenanthridine compound through ring opening cyclization of alkenyl benzotriazole under visible light catalysis

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Experimental program
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Effect test

Embodiment 1

[0031] The preparation of embodiment-2-cyano-2-methyl-3-(phenidin-6-yl) ethyl propionate

[0032] Take a Schlenk reaction tube, add a magnetic stirring bar to it, and then add 0.2 mmol of 1-(1-phenylethenyl)-1H-benzo[d][1,2,3]triazole (CAS:23269- 74-1), 0.5 mmol of 4-dimethylaminopyridine (CAS: 1122-58-3), 2 mL of 1,4-dioxane (CAS: 123-91-1), and finally 0.5 mmol of Ethyl 2-bromo-2-cyanopropionate (CAS: 26526-81-8).

[0033] After argon protection, the reaction was completed under the irradiation of 450-460 nm blue LED light for 12 h. The final product was detected by TLC and finally separated by column chromatography to obtain the final product ethyl 2-cyano-2-methyl-3-(phenidin-6-yl)propanoate with a yield of 88%. The reaction equation is as follows:

[0034]

[0035] The 1H NMR characterization of ethyl 2-cyano-2-methyl-3-(phenidin-6-yl)propanoate is as follows: 1 H NMR (400MHz, CDCl 3 )δ8.64(d,J=8.3Hz,1H),8.53(d,J=7.8Hz,1H),8.13(d,J=8.2Hz,1H),8.07(d,J=7.9Hz,1H) ,7...

Embodiment 2

[0036] Example 2 Preparation of ethyl 2-cyano-2-methyl-3-(9-methylphenidin-6-yl) propionate

[0037] Take a Schlenk reaction tube, add a magnetic stirrer to it, and then add 0.2 mmol of 1-(1-(p-tolyl)ethenyl)-1H-benzo[d][1,2,3]triazole (CAS : 1186338-74-8), 0.5 mmol of 4-dimethylaminopyridine, 2 mL of 1,4-dioxane, and finally 0.5 mmol of ethyl 2-bromo-2-cyanopropionate.

[0038] After argon protection, the reaction was completed under the irradiation of 450-460 nm blue LED light for 12 h. The final product was detected by TLC and finally separated by column chromatography to obtain the final product ethyl 2-cyano-2-methyl-3-(9-methylphenidin-6-yl)propanoate with a yield of 70%. The reaction equation is as follows:

[0039]

[0040] The 1H NMR spectrum of ethyl 2-cyano-2-methyl-3-(9-methylphenidin-6-yl)propanoate is characterized as follows: 1 HNMR (400 MHz, CDCl 3)δ8.51(d,J=8.0Hz,1H),8.42(s,1H),8.03(dd,J=12.4,8.3Hz,2H),7.73–7.57(m,2H),7.52(dq,J =8.3Hz,1H),4.37–4.29(m,2...

Embodiment 3

[0041] Example 3 Preparation of ethyl 2-cyano-2-methyl-3-(9-ethylphenidin-6-yl) propionate

[0042] Take a Schlenk reaction tube, add a magnetic stir bar to it, and then add 0.2 mmol of 1-(1-(p-ethylphenyl)vinyl)-1H-benzo[d][1,2,3]triazole (CAS: 1659293-79-4), 0.5 mmol of 4-dimethylaminopyridine, 2 mL of 1,4-dioxane, and finally 0.5 mmol of ethyl 2-bromo-2-cyanopropionate.

[0043] After argon protection, the reaction was completed under the irradiation of 450-460 nm blue LED light for 12 h. The final product was detected by TLC and finally separated by column chromatography to obtain the final product ethyl 2-cyano-2-methyl-3-(9-ethylphenidin-6-yl)propanoate with a yield of 70%. The reaction equation is as follows:

[0044]

[0045] The H NMR spectrum of ethyl 2-cyano-2-methyl-3-(9-ethylphenidin-6-yl)propionate is characterized as follows: 1 HNMR (300 MHz, CDCl 3 )δ8.54(d,J=7.7Hz,1H),8.43(s,1H),8.05(d,J=8.4Hz,2H),7.73–7.51(m,3H),4.33(q,J=7.1 Hz,2H),4.03and 3.90(ABq,J=...

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Abstract

The invention belongs to the technical field of compound preparation, and particularly relates to a synthesis method for constructing a phenanthridine compound through ring opening cyclization of alkenyl benzotriazole under visible light catalysis, which comprises the following steps: by taking alkenyl benzotriazole as shown in a formula I and tertiary alkyl bromide as shown in a formula II as raw materials, under the action of alkali and a solvent, carrying out a ring opening cyclization reaction on the alkenyl benzotriazole and tertiary alkyl bromide to obtain the phenanthridine compound. And carrying out cyclization reaction under the conditions of room temperature, inert atmosphere and illumination to synthesize the phenanthridine compound as shown in the formula III. The alkenyl benzotriazole is wide in raw material source, low in price, good in stability and capable of being stored for a long time, and the whole reaction is carried out under the illumination condition, does not need to be heated and is environmentally friendly.

Description

technical field [0001] The invention belongs to the technical field of compound preparation, in particular to a method for synthesizing phenanthrene compounds by ring-opening cyclization of alkenyl benzotriazole under visible light catalysis. Background technique [0002] Phorphine is a class of biologically active nitrogen-containing heterocyclic compounds. Such compounds have very strong biological and pharmacological activities and exist in various alkaloids, and they can be widely used in antibacterial, antifungal and antitumor fields. In the reports on the synthesis of phenanthrenes, the use of isocyanobiphenyl / alkenyl azidobiphenyl and some free radical sources as substrates is a common method by radical cycloaddition. However, this method also has some problems: the substrate has poor stability, cannot be stored for a long time, and the substrate is highly toxic. [0003] In 2013, Zhou Lei's group described a PhI(OAc) 2 As oxidant, benzoquinone (BQ) as catalyst, so...

Claims

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Application Information

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IPC IPC(8): C07D221/12
CPCC07D221/12
Inventor 李盼赵静静李嘉琪
Owner HENAN UNIVERSITY
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