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Poly-substituted pyrazoline compound and preparation method thereof

A pyrazoline and multi-substitution technology, which is applied in the field of multi-substituted pyrazoline compounds and their preparation, can solve problems such as difficulty in obtaining multi-substituted pyrazoline compounds, and achieve the effects of easy-to-obtain raw materials, mild reaction conditions, and great application prospects

Inactive Publication Date: 2012-06-27
ZHEJIANG NORMAL UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Although there are many methods for synthesizing pyrazoline compounds, these methods are difficult to obtain multi-substituted pyrazoline compounds containing active functional groups such as amino groups and carbonyl groups in the molecule, and the existence of these active functional groups is the further derivatization of pyrazoline compounds. Provides great convenience
So far, there have been no public reports on polysubstituted pyrazoline compounds containing active functional groups such as amino and carbonyl groups in the molecule.

Method used

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  • Poly-substituted pyrazoline compound and preparation method thereof
  • Poly-substituted pyrazoline compound and preparation method thereof
  • Poly-substituted pyrazoline compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] Example 1: Synthesis of 1-[2-(methylamino)phenyl]-4,5-diphenyl-4,5-dihydro-1H-pyrazole-3-carbaldehyde

[0035] The reaction formula is:

[0036]

[0037] At room temperature, add 0.218g (1.65mmol) cinnamaldehyde, 0.456g (1.5mmol) 1-methyl-3-benzylbenzotriazole bromide, 10mL THF, 2mL DMSO into a 25mL round bottom flask and stir to dissolve. Cool down to 0°C, add 0.168g (1.5mmol) potassium tert-butoxide in one go, follow up with thin-layer chromatography (developing solvent: ethyl acetate:petroleum ether=1:15), after the reaction, concentrate and recover under reduced pressure THF, 15 mL of water was added to the residue, extracted with 3×20 mL of ethyl acetate, the combined organic phases were washed with 2×20 mL of saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to recover ethyl acetate. The residue was quickly separated by column chromatography (eluent: ethyl acetate:petroleum ether=1:15) to obtain 0.3437 g of an orange...

Embodiment 2

[0038] Example 2: 1-[2-(methylamino)phenyl]-5-phenyl-4-(4-methylphenyl)-4,5-dihydro-1H-pyrazole-3-carbaldehyde synthesis

[0039] The reaction formula is:

[0040]

[0041] The α,β-unsaturated aldehyde (ketone) used is p-methylcinnamaldehyde, and other raw materials, experimental methods, and reaction conditions are the same as in Example 1. The product obtained was an orange-red oily liquid with a yield of 57.5%. 1 H NMR (400MHz, CDCl 3 ), δ(ppm): 9.78(s, 1H), 7.30-7.19(m, 3H), 7.16-7.09(m, 4H), 7.07-7.03(m, 2H), 6.95(t, J=7.8Hz, 1H), 6.67(t, J=8.1Hz, 2H), 6.47(q, J=4.8Hz, 1H), 6.43(t, J=7.8Hz, 1H), 5.46(d, J=6.1Hz, 1H) , 4.30(d, J=6.1Hz, 1H), 2.92(d, J=5.0Hz, 3H), 2.30(s, 3H); 13 C NMR (100MHz, CDCl 3 ), δ (ppm): 184.1, 147.7, 141.5, 139.6, 137.6, 137.4, 130.1, 129.5, 128.5, 127.2, 126.8, 125.6, 125.5, 118.5, 116.0, 111.6, 78.3, 55.9, 30.6, IR (21.3; KBr) cm -1 3413, 3129, 2814, 2796, 1650, 1513, 1401, 1147, 743, 701; HRMS (EI): theoretical value [M] + (C 24 h ...

Embodiment 3

[0042] Example 3: 4-(4-methoxyphenyl)-1-[2-(methylamino)phenyl]-5-phenyl-4,5-dihydro-1H-pyrazole-3-carbaldehyde Synthesis

[0043] The reaction formula is:

[0044]

[0045] The α,β-unsaturated aldehyde (ketone) used is p-methoxycinnamaldehyde, and other raw materials, experimental methods, and reaction conditions are the same as in Example 1. The product obtained was an orange-red oily liquid with a yield of 60.4%. 1 H NMR (400MHz, CDCl 3 ), δ(ppm): 9.77(s, 1H), 7.28-7.18(m, 3H), 7.11(d, J=6.8Hz, 2H), 7.07(d, J=8.6Hz, 2H), 6.94(t , J=7.8Hz, 1H), 6.84(d, J=8.8Hz, 2H), 6.70-6.64(m, 2H), 6.48(q, J=4.6Hz, 1H), 6.42(t, J=7.6Hz , 1H), 5.44(d, J=6.1Hz, 1H), 4.28(d, J=6.1Hz, 1H), 3.70(s, 3H), 2.91(d, J=4.3Hz, 3H); 13 C NMR (100MHz, CDCl 3 ), δ (ppm): 184.2, 159.2, 147.8, 141.5, 139.6, 132.5, 129.5, 128.5, 128.4, 126.8, 125.6, 125.5, 118.4, 116.0, 114.7, 111.6, 78.3, 55.6, 55.4, 30.5; )cm -1 3428, 3129, 2788, 1648, 1510, 1401, 1148, 741, 699; HRMS (EI): theoretical value [M...

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Abstract

The invention discloses a poly-substituted pyrazoline compound and a preparation method thereof. The structural formula of the poly-substituted pyrazoline compound disclosed by the invention is shown in the specifications, wherein R1 is one of straight chain or branch chain alkyl substituents such as methyl, ethyl, isopropyl, benzyl and the like; R2 is one of vinyl, substituted vinyl, aryl, substituted aryl and a heteromatic substituent; R3 is one of straight chain or branch chain alkyl substituents such as hydrogen, methyl, ethyl, propyl, butyl and the like; and Ar is aryl, substituted aryl and a heteromatic substituent. The preparation method of the poly-substituted pyrazoline compound comprises the following steps of: reacting 1,3-disubstituted benzotriazole salt with alkali in situ to form 1,3-disubstituted benzotriazole nitrogen ylide; and further reacting with alpha,beta-unsaturated aldehyde or alpha,beta-unsaturated ketone to obtain a polysubstituted pyrazoline compound.

Description

technical field [0001] The invention relates to the field of organic chemistry, in particular to a polysubstituted pyrazoline compound and a preparation method. Background technique [0002] Pyrazolines are an important class of nitrogen-containing five-membered heterocyclic compounds. Most pyrazoline compounds have biological activities and anti-inflammatory (Tetrahedron Lett., 2004, 45, 8523-8526) analgesia, weeding and insecticide (Chemical Journal of Chinese Universities, 1998, 19, 232-236) and other pharmacological effects; polyaryl substituted pyrazolines also have excellent optical properties, often used as optical Luminescent materials (Chemical Journal of Chinese Universities, 2006, 27, 1058-1061), used in textiles, decorative materials, protective packaging materials, fluorescent anti-counterfeiting materials, drug tracers, molecular probes, optical shutters, video media, radiation measurement Information storage elements in meters and computers (Chemical Journal...

Claims

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Application Information

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IPC IPC(8): C07D231/06
Inventor 肖孝辉仝水田柯丽丽叶小莹华巧娜莫海蓝
Owner ZHEJIANG NORMAL UNIVERSITY
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