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Application of fluoro-diphenyl sulfimide as nitrogen heterocyclic Diels-Alder reaction catalyst

A bisbenzenesulfonimide and catalyst technology, which is applied in the new application field of fluorobisbenzenesulfonimide, can solve the problems that have not been seen in application reports, and achieve the advantages of simple and fast operation, low environmental pollution and low production cost Effect

Inactive Publication Date: 2010-08-11
SOUTHWEST UNIVERSITY
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

But so far, there is no report on the application of N-F electrophilic fluorinating reagent - fluorobisbenzenesulfonimide (NFSI) as a catalyst for the aza Diels-Alder reaction.

Method used

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  • Application of fluoro-diphenyl sulfimide as nitrogen heterocyclic Diels-Alder reaction catalyst
  • Application of fluoro-diphenyl sulfimide as nitrogen heterocyclic Diels-Alder reaction catalyst
  • Application of fluoro-diphenyl sulfimide as nitrogen heterocyclic Diels-Alder reaction catalyst

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Embodiment Construction

[0016] In order to make the object, technical solution and advantages of the present invention clearer, preferred embodiments of the present invention are described in detail below.

[0017] The fluorinated bisbenzenesulfonimide used in the preferred embodiment is purchased from Tianjin Jiuri Chemical Industry Co., Ltd., and the reaction starting raw material cyclohexenone, substituted benzaldehyde and substituted aniline and other reagents are commercial reagents and have not been used. Further purification. The structure of the product was confirmed by NMR spectroscopy. In order to facilitate the comparison of results, the room temperature in the method was controlled at 25±1°C.

[0018] 1. Catalyst type and reaction condition optimization for aza Diels-Alder reaction

[0019] The present invention first takes cyclohexenone, nitrobenzaldehyde and p-methoxyaniline as model compound, the kind of catalyst (N-F electrophilic fluorinating reagent) and reaction conditions (react...

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Abstract

The invention discloses an application of fluoro-diphenyl sulfimide as a nitrogen heterocyclic Diels-Alder reaction catalyst and has the advantages of high catalytic activity, good three-dimensional selectivity, low cost, easy acquisition, and the like. The invention also provides a method for synthesizing an iso-quinuclidine compound (I) by using the fluoro-diphenyl sulfimide as the nitrogen heterocyclic Diels-Alder reaction catalyst and catalyzing cyclonene, aromatic aldehyde (ii) and aromatic amine (iii) in an inorganic solvent or an organic solvent to carry out a nitrogen heterocyclic Diels-Alder reaction. The invention has the advantages of simple, convenient and rapid operation, high product yield, good three-dimensional selectivity, less environmental pollution, low production cost, and the like, thereby having good prospects.

Description

technical field [0001] The invention relates to a new application of fluorobisbenzenesulfonimide, in particular to the application of fluorobisbenzenesulfonimide as an aza Diels-Alder reaction catalyst. Background technique [0002] Isoquinucidine (3-azabicyclo [2.2.2] octane) is the basic structural unit of many active compounds (including natural compounds and synthetic compounds), for example, the basic structure of the alkaloid ibogaine (ibogaine) The unit is isoquinucidine, and ibogaine has been confirmed by research to have a detoxification effect, which can reduce the self-intake of cocaine and morphine and alleviate the withdrawal symptoms of morphine. The most direct method of synthesizing isoquinucidine compounds is to adopt the aza Diels-Alder reaction (that is, imine compounds and conjugated diene compounds undergo 1,4 addition reactions to generate six-membered ring compounds), but the current There are few literature reports on this aspect. In the existing rep...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): B01J31/02C07D453/06
Inventor 官智何延红吴狄
Owner SOUTHWEST UNIVERSITY
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