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Thiophene macrocyclic compound and preparation method for its derivant

A technology for macrocyclic compounds and cyclic compounds, applied in the direction of organic chemistry, etc., can solve the problem of no progress in the preparation method of thiophene twelve-membered cyclic compound 2, and achieve the effects of improving the preparation yield and increasing the solubility.

Inactive Publication Date: 2009-01-14
HENAN UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

This patented technology allows for efficient production of certain types of chemical substances called beta -thienes such as tenthionine or cathinone by reacting them with specific reactive agents under special circumstances like hydrolysis without water. By adding these reagents together during this step, there will be more stable molecules formed due to their strong interactions between each others. Overall, this new technique provides technical benefits over existing techniques while maintaining its efficiency and effectiveness across various applications.

Problems solved by technology

This patented technical problem addressed in this patents relates to improving the efficiency at producing certain types of chemical substances called cyclodimers or cis/transfer dimer systems containing sixteen membered rings. Current processes involve expensive reagents like Grignard Reagent, Lithium Intermediate Exchanger, Fetrilm Group Compound, Diphenol Chelating Ligand Exchange Method, Sulfur Trioxane Cyclotronics Using Microcavity Gravimetrics Technique, Different Technologies were developed overall, these techniques aim to increase production rates while reducing costs associated with current methods.

Method used

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  • Thiophene macrocyclic compound and preparation method for its derivant
  • Thiophene macrocyclic compound and preparation method for its derivant
  • Thiophene macrocyclic compound and preparation method for its derivant

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Embodiment Construction

[0049] The preparation method of the present invention is as follows:

[0050] (1) Preparation of compound 3 (2,2'-dibromo-5,5'-bis(trimethylsilyl)-[3,3']-bithiophene)

[0051] First add 37.5mmol of n-butyllithium to 38.9mmol of diisopropylamine in ether solution, prepare LDA solution at 0℃, and add this LDA solution dropwise to 2,2'-dibromo-[ 3,3']-Bithiophene (5.44g, 16.8mmol) was reacted in ether solution for 2 hours. The temperature of the reaction solution was lowered to -70-80°C, 85.1 mmol of trimethylchlorosilane was dropped into the reaction solution, and the temperature was slowly raised to room temperature. The reaction system was quenched with water, extracted with ether, washed with water, and dried, and then the crude product was subjected to silica gel column chromatography using petroleum ether (60-90° C.) as the eluent to isolate compound 3 (7.00 g, 89.1%). The conditions of the other two parallel reactions are as follows: 4.44 g and 5.79 g of raw materials are use...

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Abstract

The invention relates to a thiophene macrocyclic compound and a preparation method of derivatives of the thiophene macrocyclic compound, in particular to a preparation method of a thiophene eight membered cyclic compound and a thiophene twelve membered cyclic compound. The preparation method is as follows: 2, 2`-dibromo-[3, 3`]-bithiophene is adopted as the raw material; lithium diisopropylamide (LDA) is firstly used to capture the Alpha- proton, then the 2, 2`-dibromo-[3, 3`]-bithiophene is quenched by trimethylchlorosilane, and a compound 3 is prepared; then the compound 3 and butyl lithium generate bromine and lithium exchanging reaction, and copper chloride oxidative cyclization is used to generate thiophene eight membered cyclic compound 4 and thiophene twelve membered cyclic compound 5, wherein, the yield of the compound 5 reaches up to 36 percent; and in the condition that trifluoroacetic exists, the compound 4 and the compound 5 remove TMS, and a compound 1-four (2,3-bithiophene) and a compound 2-six (2,3-bithiophene) are obtained. The preparation method of the derivatives of the thiophene macrocyclic compound realizes the aim of preparing the thiophene eight-membered cyclic compound at high yield, and most importantly, the preparation method realizes the aim of preparing the thiophene twelve-membered cyclic compound at high yield, and the total yield of the three steps reaches up to 27 percent. The synthetic process of the method has operability, and the reaction conditions of waterless, oxygen free and low-temperatured. Thus, the preparation method is suitable for scale preparation.

Description

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Claims

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Application Information

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Owner HENAN UNIVERSITY
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