Method of simple catalysis to prepare spiro-1,3-dioxoindanpyrane derivative and catalyst for preparing same

A technology of pyran derivatives and dioxindene, which is applied in organic compound/hydride/coordination complex catalysts, physical/chemical process catalysts, chemical instruments and methods, etc. Large usage, not easy to biodegrade and other problems, to achieve the effect of more recycling times, less environmental hazards, and easy promotion and application

Active Publication Date: 2017-08-29
东营睿港投资服务有限责任公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] The purpose of the present invention is to overcome the large amount of catalyst used, less recyclable times, difficult biodegradation and Due to the shortcomings of complex reaction operations, etc., a method for the simple and easy catalytic preparation of spirocyclic 1,3-dioxoindan pyran derivatives and a catalyst for its preparation are provided

Method used

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  • Method of simple catalysis to prepare spiro-1,3-dioxoindanpyrane derivative and catalyst for preparing same
  • Method of simple catalysis to prepare spiro-1,3-dioxoindanpyrane derivative and catalyst for preparing same
  • Method of simple catalysis to prepare spiro-1,3-dioxoindanpyrane derivative and catalyst for preparing same

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preparation example Construction

[0032] For the preparation method of the above-mentioned catalyst used in the present invention, see the related literature (Introduction of a novel basic ionic liquid containing dual basic functional groups for the efficient synthesis of spiro-4H-pyrans[J], Journal of Molecular Liquids, 2016, 224: 1092 ~ 1101 ).

[0033] The specific process of the method for preparing spirocyclic 1,3-dioxoindanpyran derivatives in the present invention is: adding ninhydrin, malononitrile, 1,3-cyclohexanedione compound and catalyst to ethanol respectively In the aqueous solution, and mixed uniformly, the molar ratio of ninhydrin (1), malononitrile (2) and 1,3-cyclohexanedione compound (3) in the above reaction raw materials is 1:(1~1.2):1 , The 1,3-cyclohexanedione compound is 1,3-cyclohexanedione, 5,5-dimethyl-1,3-cyclohexanedione, barbituric acid, 1,3-dimethyl Any one of ylbarbituric acid, 4-hydroxycoumarin and 8-hydroxyquinoline; the molar amount of the catalyst is 3 to 6% of the molar amoun...

Embodiment 1

[0040] Add 1mmol ninhydrin, 1mmol malononitrile, 1mmol 1,3-cyclohexanedione and 0.04mmol catalyst respectively into a 50ml single-necked flask with a stir bar and a condenser containing 4ml 92% ethanol aqueous solution. React at ℃ for 10 minutes, the reaction pressure is one atmosphere, and perform TLC (Thin Plate Chromatography) tracking. After the reaction is completed, cool to room temperature, crush the precipitated solid, stand, and filter with suction. The filter residue is washed with 92% ethanol aqueous solution and dried in vacuo Obtain 2'-amino-3'-cyano-1,3,5'-trioxo-5',6',7',8'-tetrahydrospirocyclic indanpyranobenzene, the yield is 92%, the filtrate after 4ml was made up with washing liquid, and ninhydrin, malononitrile and 1,3-cyclohexanedione were directly added for repeated use.

[0041] The 2'-amino-3'-cyano-1,3,5'-trioxo-5',6',7',8'-tetrahydrospirocyclic indane pyranobenzene obtained in this example The performance parameters are as follows: IR (KBr): 3402, 3315,...

Embodiment 2～4

[0044] A different reaction temperature (shown in Table 1) was adopted to replace the reaction temperature described in Example 1. Other conditions were the same as in Example 1. The experimental results are shown in Table 1, and the 2'-amino-3' obtained in Examples 2 to 4 The performance parameters of -cyano-1,3,5'-trioxo-5',6',7',8'-tetrahydrospiroindanpyranobenzene are similar to those of Example 1.

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Abstract

The invention discloses a method of simple catalysis to prepare a spiro-1,3-dioxoindanpyrane derivative and a catalyst for preparing same and belongs to the technical field of chemical material preparation. In the preparation method, the molar ratio of ninhydrin, malononitrile and a 1,3-cyclohexanedione compound is 1:1-1.2:1, wherein the molar percentage of the catalyst is 3-6% by mole of the ninhydrin. The volume quantity of a reaction solvent, an ethanol water solution, is 4-7 times of the molar weight of the ninhydrin. Reaction temperature is 74-80 DEG C and reaction time is 8-24 min. After the reaction is finished, the reaction product is cooled to room temperature and is subjected to suction filtration. A filter residue is washed through an ethanol water solution and is vacuum-dried to obtain the spiro-1,3-dioxoindanpyrane derivative. Compared with the prior art, the catalyst is low in use amount and has more recycling utilization times. The whole preparation process is simple and convenient in operations and has high green degree, so that the method is easy to apply in industrial large-scale production.

Description

Technical field [0001] The invention belongs to the technical field of chemical material preparation, and specifically relates to a method for simply catalyzing the preparation of spirocyclic 1,3-dioxoindan pyran derivatives and a catalyst for preparation thereof. Background technique [0002] Due to the unique structure and properties of spiro derivatives, their applications in asymmetric catalysis, luminescent materials, photochromic materials, medicines, pesticides, and polymer adhesives have attracted more and more attention in recent years. The substances containing spiro heterocyclic structures are important fragments of many drugs and natural alkaloids due to their high pharmacological and biological activities. Therefore, it is of great significance to study the preparation of spirocyclic 1,3-dioxoindan pyran derivatives containing spiro heterocyclic structures. [0003] In the prior art, proline, PEG-400, ammonium chloride, ethylenediamine diacetic acid, benzyltriethylamm...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): B01J31/02C07D311/96C07D491/107C07D493/10C07D519/00
CPCB01J31/0244C07D311/96C07D491/107C07D493/10C07D519/00
Inventor 卢华沈智培
Owner 东营睿港投资服务有限责任公司
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