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O-alkenyl aromatic nitrile compound and preparation method thereof

A compound and aromatic nitrile technology, applied in the field of o-alkenyl aromatic nitrile compounds and their preparation, can solve the problems of high cost and complex synthesis method, and achieve the effects of simple and efficient synthesis, good atom economy and step economy

Active Publication Date: 2020-02-28
GUANGDONG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] In view of this, the application provides a kind of o-alkenyl aromatic nitrile compound and preparation method thereof, effectively solve the existing conventional method of synthesizing o-alkenyl aromatic nitrile compound There are technical problems of complex synthesis method and high cost

Method used

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  • O-alkenyl aromatic nitrile compound and preparation method thereof
  • O-alkenyl aromatic nitrile compound and preparation method thereof
  • O-alkenyl aromatic nitrile compound and preparation method thereof

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preparation example Construction

[0060] The application discloses that the preparation method of o-alkenyl aromatic nitrile compound preferably comprises the following steps: under an atmosphere of atmospheric pressure oxygen, add imidate derivatives (0.1 mmol) shown in formula (II) successively in the reactor, Then add 2.5 mg of dichloro(pentamethylcyclopentadienyl) rhodium dimer, 7.8 mg of bistrifluoromethanesulfonimide silver salt, 4.9 mg of sodium acetate and 12.0 mg of copper acetate, injecting (III) A solution of the alkene compound (0.2 mmol) in 1,2-dichloroethane (1.0 mL) was placed in a reactor at 100° C. for 12 h, The end of the reaction was confirmed by thin-layer chromatography analysis. After the reaction solution was filtered through diatomaceous earth, it was concentrated by rotary evaporation with 400 mesh silica gel to make a dry powder, and then the reaction product was separated by column chromatography. The 400 mesh silica gel was 10 grams, and the developer was volume Petroleum ether an...

Embodiment 1

[0064] The present embodiment carries out the preparation of (E)-2-(3-bromostyryl)-benzonitrile (1a), and its reaction formula is as follows:

[0065]

[0066] Under an atmosphere of oxygen at atmospheric pressure, the formula is added successively in the reactor to add 2.5mg dichloro(pentamethylcyclopentadienyl) rhodium dimer, 7.8mg bistrifluoromethanesulfonylimide silver salt, 4.9 mg sodium acetate and 12.0 mg copper acetate, followed by adding imidate derivative 2a (14.9 mg, 0.1 mmol) shown in formula (II), and injecting olefin compound 3a (36.2 mg, 0.2 mmol) shown in formula (III) with a syringe ) solution of 1,2-dichloroethane (1.0mL) in the reactor and placed at 100°C for 12h, the end of the reaction was confirmed by thin-layer chromatography analysis, the reaction solution was filtered through diatomaceous earth and filtered through 400 mesh The silica gel is concentrated by rotary evaporation to make a dry powder, and then the reaction product is separated by column...

Embodiment 2

[0070] This embodiment carries out the preparation of (E)-2-(4-tert-butylstyryl)-4-fluorobenzonitrile (1b), and its reaction formula is as follows:

[0071]

[0072] Under an atmosphere of oxygen at atmospheric pressure, the formula is added successively in the reactor to add 2.5mg dichloro(pentamethylcyclopentadienyl) rhodium dimer, 7.8mg bistrifluoromethanesulfonylimide silver salt, 4.9 mg sodium acetate and 12.0 mg copper acetate, then add the imidate derivative 2b (16.7mg, 0.1mmol) shown in formula (II), and inject the olefin compound 3b (32.0mg, 0.2mmol) shown in formula (III) with a syringe ) solution of 1,2-dichloroethane (1.0mL) in the reactor and placed at 100°C for 12h, the end of the reaction was confirmed by thin-layer chromatography analysis, the reaction solution was filtered through diatomaceous earth and filtered through 400 mesh The silica gel is concentrated by rotary evaporation to make a dry powder, and then the reaction product is separated by column ch...

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Abstract

The invention belongs to the technical field of organic synthesis, and particularly relates to an o-alkenyl aromatic nitrile compound and a preparation method thereof. The o-alkenyl aromatic nitrile compound provided by the invention has a structural formula as shown in a formula (I) which is described in the specification. The invention also provides the preparation method of the o-alkenyl aromatic nitrile compound. The preparation method comprises the following steps: dissolving a compound as shown in the formula (II) which is described in the specification and a compound as shown in a formula (III) which is described in the specification in an inert solvent, and carrying out a reaction under alkaline conditions under the actions of an oxidant and a metal catalyst to obtain the o-alkenylaromatic nitrile compound. The method disclosed by the invention has the advantages of good functional group compatibility and wide substrate range, can be applied to regioselective introduction of two functional groups, namely a cyano group and alkene into naphthalene, indole and the like, is applicable to later modification of drug molecules including probenecid and the like, presents importantapplication potential, and effectively solves the technical problem that conventional methods for synthesizing the o-alkenyl aromatic nitrile compound are complex.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to an o-alkenyl aromatic nitrile compound and a preparation method thereof. Background technique [0002] Nitriles have versatile utility and are widely used in organic synthesis, pharmaceuticals, and chemical industries. In the traditional field of organic synthesis, nitriles are also used as precursors or intermediates of imines, ketones, amides, esters, alcohols, and amines. Based on the special properties of the cyano functional group, nitrile also plays an important role in clinical drugs, pesticides and dyes. The linear structure of the carbon-nitrogen triple bond of the cyano functional group of the nitrile, and its occupied size is only one-eighth of the methyl group, which also allows the cyano group to easily penetrate into the target molecule. [0003] In view of the diversity of the reactivity of the cyano functional group, the reactions of aryl n...

Claims

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Application Information

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IPC IPC(8): C07C253/06C07C255/50C07C255/52C07C303/40C07C311/16C07D209/08C07D333/38
CPCC07C253/06C07C255/50C07C255/52C07C303/40C07C311/16C07D209/08C07D333/38
Inventor 饶建行李先纬欧阳文森
Owner GUANGDONG UNIV OF TECH
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