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Ring opening method of aziridine compounds

A technology of aziridine and compounds, applied in the field of organic synthesis, can solve problems such as low selectivity, high catalyst price, and long reaction time, and achieve high regioselectivity, high yield, and low price

Inactive Publication Date: 2014-07-09
TAIYUAN UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In summary, although some progress has been made in the research on the ring-opening reaction of bromine-containing compounds to aziridine, there are generally disadvantages such as high catalyst price, long reaction time, and low selectivity. The nucleophile reacts with aziridine for ring opening to make the reaction easier to operate, more environmentally friendly, with higher yield and stronger selectivity. It is worthy of further exploration and discovery

Method used

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  • Ring opening method of aziridine compounds
  • Ring opening method of aziridine compounds
  • Ring opening method of aziridine compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Into a 50 mL round bottom flask was added 1 mmol of the aziridine compound of the structural formula 1a in Table 1, 0.4 mmol of ferric bromide, and 10 mL of dichloromethane, and stirred at room temperature 25°C for 0.5 h. After the reaction was completed, the concentrated solvent reaction system was purified by silica gel column chromatography to obtain the ring-opened product 3a as a white solid (eluent: petroleum ether: ethyl acetate = 5:1).

[0035] The regioselectivity of the ring-opening product was very high, and only the product of the structural formula 3a in Table 1 was obtained. The structure of the product was confirmed by infrared spectroscopy and NMR characterization, and the results are listed in Table 1.

[0036] The reaction of table 1 aziridine compound 1a and ferric bromide

[0037]

[0038] 3a:R f =0.2(Petroleum ether / AcOEt=5 / 1v / v);White solid;Mp:95-96℃;IR(KBr,cm -1 )3265(NH),1334,1155(S=O); 1 HNMR (600MHz, CDCl 3 ):δ2.44(s,3H),3.40-3.50(m,2H),...

Embodiment 2

[0040] Add 0.2mmol of the aziridine compound of the structural formula 1b in Table 2, 0.24mmol of sodium bromide, and 2.5mL of dichloromethane into the test tube, and stir at 20°C for 0.2h. After the reaction was completed, the concentrated solvent reaction system was purified by silica gel column chromatography to obtain the ring-opened product 3b as a white solid (eluent: petroleum ether: ethyl acetate = 5:1).

[0041] The regioselectivity of the ring-opening product is very high, and only the product of the structural formula 3b in Table 2 was obtained. The product was characterized by infrared spectroscopy, nuclear magnetic resonance and high-resolution mass spectrometry, and the structure of the product was confirmed. The results are listed in Table 2.

[0042] The reaction of table 2 aziridine compound 1b and sodium bromide

[0043]

[0044] 3b:R f =0.2(Petroleum ether / AcOEt=5 / 1v / v);White solid;Mp115-117℃;IR(KBr,cm -1 )3283,3064,2924,2854,1595,1490,1407,1329,1212,11...

Embodiment 3

[0046] In a 50 mL round bottom flask, 1 mmol of the aziridine compound of the structural formula 1c in Table 3, 1.1 mmol of potassium bromide, and 5 mL of dichloromethane were added, and the reaction was stirred at 25° C. for 0.1 h. After the reaction was completed, the concentrated solvent reaction system was purified by silica gel column chromatography to obtain the ring-opened product 3c as a white solid (eluent: petroleum ether: ethyl acetate = 5:1).

[0047] The regioselectivity of the ring-opening product is very high, and only the product with the structural formula 3c in Table 3 was obtained. The product was characterized by infrared spectroscopy, nuclear magnetic resonance and high-resolution mass spectrometry, and the structure of the product was confirmed. The results are listed in Table 3.

[0048] The reaction of table 3 aziridine compound 1c and potassium bromide

[0049]

[0050] 3c:R f =0.12(Petroleum ether / AcOEt=5 / 1v / v);White solid;Mp88-90℃;IR(KBr,cm -1 )...

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Abstract

The invention discloses a ring opening method of aziridine compounds, particularly a ring opening method of aziridine compounds in different structures by using metal bromide, belonging to the technical field of organic synthesis. The aziridine compound is subjected to ring opening reaction by using tosyl-activated aziridine compounds as the initial raw material, dichloromethane as a solvent and bromine in the metal bromide as a nucleophilic reagent. The method has the advantages of simple reaction process, mild conditions and wide applicability, can obtain higher yield for aziridine compounds in different structures, has very high regioselectivity, and can form a single isomer from most aziridine compounds.

Description

technical field [0001] The invention relates to a ring-opening method for aziridine compounds, in particular to a ring-opening method for aziridine compounds with different structures by using metal bromides, and belongs to the technical field of organic synthesis. Background technique [0002] Aziridine compounds are important building blocks and intermediates in organic synthesis. They exist in many natural products and have good antiviral, antitumor and other biological activities. Aziridine can undergo a series of important reactions, such as ring-opening reaction, cycloaddition reaction, reduction and elimination reaction, etc. Its nucleophilic ring-opening reaction can be used to synthesize β-substituted amino compounds, and then synthesize many compounds such as amino alcohols, amino acids, alkaloids and β-lactamides that have biological activity and have extremely promising application prospects in the pharmaceutical and chemical industries. [0003] The nucleophili...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C311/16C07C303/40C07C311/17C07C311/20C07B43/04
Inventor 李兴魏文珑张莉常宏宏李彦威
Owner TAIYUAN UNIV OF TECH
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