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Bi-heterocycle aldolase-2,8-diamino-Troger's Base Schiff base catalyst and preparation method

A -base, two-heterocycle technology, applied in the field of biheterocyclic aldehyde acetal -2,8-diamino-Base Schiff base catalyst and preparation, to achieve the effects of enhancing alkalinity, improving yield and high selectivity

Inactive Publication Date: 2018-11-02
XUZHOU NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] How to combine catalytically active imines with TB to obtain a class of TB derivatives with higher catalytic activity has not been reported in the literature

Method used

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  • Bi-heterocycle aldolase-2,8-diamino-Troger's Base Schiff base catalyst and preparation method
  • Bi-heterocycle aldolase-2,8-diamino-Troger's Base Schiff base catalyst and preparation method
  • Bi-heterocycle aldolase-2,8-diamino-Troger's Base Schiff base catalyst and preparation method

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0035] Embodiment 1: preparation compound 4a

[0036] Intermediate 2 (1.0mmol), 2-thiophenecarbaldehyde (1.2mmol), triethylamine (1mol%) and absolute ethanol (5mL) were successively added to a 50mL dry round-bottomed flask, refluxed at 80°C for 12h, and the reaction was completed ( TLC track), filter, evaporate excess solvent under reduced pressure, crude product is passed through column chromatography (V 石油醚 :V 乙酸乙酯 =1:9 gradient elution) separation to obtain compound 4a with a yield of 93%.

[0037] The structural formula of compound 4a is:

[0038] The molecular formula is: C 27 h 25 N 4 S 2

[0039] Chinese name: (1E,1'E)-N,N'–(4,10-dimethyl-6H,12H-5,11-methylenedibenzo[b,f][1,5] Diazaoctine-2,8-diyl)bis(1-(thien-2-yl)methimine)

[0040] English name: (1E,1'E)-N,N'-(4,10-dimethyl-6H,12H-5,11-methanodibenzo[b,f][1,5]diazocine-2,8-diyl )bis(1-(thiophen-2-yl)methanimine)

[0041] Appearance: yellow solid

[0042] Melting point: 212.5-214.2°C

[0043] Proton NMR...

Embodiment 2

[0046] Embodiment 2: preparation compound 4b

[0047] Add intermediate 2 (1.0mmol), 3-methylthiophene-2-carbaldehyde (1.2mmol), triethylamine (1mol%) and absolute ethanol (5mL) successively into a 50mL dry round bottom flask, and reflux at 80°C 12h, the reaction finishes (TLC follow-up), filters, evaporates excess solvent under reduced pressure, and crude product is passed through column chromatography (V 石油醚 :V 乙酸乙酯 =1:9 gradient elution) separation to obtain compound 4b with a yield of 91%.

[0048] The structural formula of compound 4b is:

[0049] The molecular formula is: C 29 h 29 N4 S 2

[0050] Chinese name: (1E,1'E)-N,N'-(4,10-dimethyl-6H,12H-5,11-methylenedibenzo[b,f][1,5 ]diazaoctine-2,8-diyl)bis(1-(3-methyl-thiophen-2-yl)methimine)

[0051] English name: (1E,1'E)-N,N'-(4,10-dimethyl-6H,12H-5,11-methanodibenzo[b,f][1,5]diazocine-2,8-diyl )bis(1-(3-methyl-thiophen-2-yl)methanimine)

[0052] Appearance: yellow solid

[0053] Melting point: 231.6-233.8°C ...

Embodiment 3

[0057] Embodiment 3: preparation compound 4c

[0058] Add intermediate 2 (1.0mmol), 5-methylthiophene-2-carbaldehyde (1.3mmol), triethylamine (1mol%) and absolute ethanol (5mL) successively into a 50mL dry round bottom flask, and reflux at 80°C 12h, the reaction finishes (TLC follow-up), filters, evaporates excess solvent under reduced pressure, and crude product is passed through column chromatography (V 石油醚 :V 乙酸乙酯 =1:9 gradient elution) separation to obtain compound 4c with a yield of 88%.

[0059] The structural formula of compound 4c is:

[0060] The molecular formula is: C 29 h 29 N 4 S 2

[0061] Chinese name: (1E,1'E)-N,N'-(4,10-dimethyl-6H,12H-5,11-methylenedibenzo[b,f][1,5 ]diazaoctine-2,8-diyl)bis(1-(5-methyl-thiophen-2-yl)methimine)

[0062] English name: (1E,1'E)-N,N'-(4,10-dimethyl-6H,12H-5,11-methanodibenzo[b,f][1,5]diazocine-2,8-diyl )bis(1-(5-methyl-thiophen-2-yl)methanimine)

[0063] Appearance: yellow solid

[0064] Melting point: 178.3-179.9°C...

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Abstract

The invention discloses a bi-heterocycle aldolase-2,8-diamino-Troger's Base Schiff base catalyst and a preparation method. The structural formula of the Schiff base catalyst is disclosed in a formula4. The Schiff base catalyst is prepared by the following main preparation steps: taking 4-nitro-2-toluidine and paraformaldehyde as starting raw materials; through Henry reaction, asymmetric Michael addition reaction, nitro-reduction reaction and aldimine condensation reaction, obtaining a target product. The synthesis route of the Schiff base catalyst is simple, the reaction condition of each step is moderate, yield is effectively improved, and the prepared Schiff base catalyst has high catalytic activity and high selectivity. The formula is shown in the description.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and relates to the synthesis of a Schiff base catalyst, in particular to a bis-heterocyclic acetal-2,8-diamino- Base Schiff base catalyst and preparation method. Background technique [0002] base(TB) is the first N-centered chiral compound synthesized. Due to its unique structural characteristics, it has many advantages as an organic catalyst, such as dual chirality, multiple catalytic active sites, and suitable dihedral angles. , great molecular rigidity, etc. TB is an excellent candidate framework for organic base catalysts with strong catalytic activity and high selectivity. [0003] Imines are obtained by the condensation of primary amines and carbonyl compounds, and can coordinate with metal ions. They are one of the most widely used organic compounds and have a wide range of applications in analytical chemistry, biochemistry, inorganic chemistry, medicine, materials and many...

Claims

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Application Information

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IPC IPC(8): B01J31/02C07D487/08
CPCB01J31/0241C07D487/08
Inventor 任璇璇苑睿房樾陈雯宛瑜吴翚
Owner XUZHOU NORMAL UNIVERSITY
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