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Pyridine-fused norcarbrole compound and preparation method thereof

A technology for pyridine fusion and compound, which is applied in the field of pyridine fusion norcarbrole compound and its preparation, can solve the problems that have not been reported in the literature, and achieve the effects of good reaction selectivity, simple and economical operation, and high yield

Active Publication Date: 2019-05-14
HUNAN UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] At present, there is no literature report about the method of pyridine-fused norcarbrole

Method used

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  • Pyridine-fused norcarbrole compound and preparation method thereof
  • Pyridine-fused norcarbrole compound and preparation method thereof
  • Pyridine-fused norcarbrole compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Weigh aminonorcarbrole (18mg, 0.03mmol) and 4-methoxybenzaldehyde (0.18mmol) in 35mL capped tube reactor, add new distilled toluene (3ml) in above-mentioned reactor, in the presence of oxygen Under the conditions of 110 ° C stirring reaction for 8 hours, follow the reaction with thin layer chromatography (TLC), after the reaction is complete, cool to room temperature, use 200-300 mesh silica gel for column chromatography, and use a volume ratio of 1:1 or 1 : 2 mixed solvents of dichloromethane and normal hexane as eluent, collect the solution of the 2nd elution point, the collected solution obtains dark brown product after concentrating and drying, promptly gets the product pyridine fused norcarba azole compound, the yield is 74%.

[0027] Spectrum characterization data are as follows: 1 H NMR (500MHz, CDCl 3 ,298K) δ: -0.69(d,J=4.0Hz,2H,pyrrH),1.07(d,J=4.0Hz,2H,pyrrH),1.21(d,J=4.0Hz,2H,pyrrH),1.76( s,6H,-CH 3 ),1.77(s,6H,-CH 3 ),1.79(d,J=4.0Hz,2H,pyrrH),1.92(d,J=5...

Embodiment 2

[0030] In this example, the same synthesis process as in Example 1 was adopted, and the raw material was changed to terephthalaldehyde in an amount of 0.18 mmol to obtain a dark brown product, that is, the product pyridine-fused norcarbrole compound with a yield of 73%.

[0031] Product spectral characterization data are as follows: 1 H NMR (500MHz, CDCl 3 ,298K)δ:-1.01(d,J=4.0Hz,2H,pyrrH),1.07(d,J=4.0Hz,2H,pyrrH),1.11(d,J=5.0Hz,2H,pyrrH),1.76( s,6H,-CH 3 ),1.78(br,6H(-CH 3 )+2H(pyrrH)), 1.92(d, J=5.0Hz, 2H, pyrrH), 2.11(d, J=5.0Hz, 2H, pyrrH), 2.16(s, 12H, -CH 3 ),2.59(s,12H,-CH 3 ), 5.74(d, J=9.0Hz, 2H, ArH), 5.85(s, 4H, ArH), 6.17(s, 4H, ArH), 6.76(d, J=9.0Hz, 2H, ArH), 9.09( s,1H,-CHO); 13 C NMR (125MHz, CDCl 3 ,298K)δ:17.60(-CH 3 ),17.64(-CH 3 ),20.5(-CH 3 ),20.9(-CH 3 ),114.2(pyrrC),114.3(pyrrC),117.9(pyrrC),120.0,121.8(pyrrC),122.5(pyrrC),125.6,125.7,127.4,127.5,127.7,127.9,132.3,133.4,134.6,134.7,135 (pyrrC), 136.8, 139.0, 148.0, 148.2, 148.4, 149.4, 153.8,...

Embodiment 3

[0034] This example uses basically the same synthesis process as Example 1, the raw material is changed to 3,4,5-trimethoxybenzaldehyde, the dosage is 0.18mmol, and the dark brown product is obtained, namely the product pyridine-fused norcarbrole compound , the yield was 80%.

[0035] Product spectral characterization data are as follows: 1 H NMR (500MHz, CDCl 3 ,298K) δ: -0.45(d,J=4.0Hz,2H,pyrrH),1.06(d,J=3.5Hz,2H,pyrrH),1.21(d,J=4.0Hz,2H,pyrrH),1.78( s,12H(-CH 3 )+2H(pyrrH)), 1.91(d, J=4.5Hz, 2H, pyrrH), 2.10(d, J=4.5Hz, 2H, pyrrH), 2.15(s, 12H, -CH 3 ),2.62(s,12H,-CH 3 ),2.84(s,3H,-OCH 3 ),3.58(s,6H,-OCH 3 ),4.65(s,2H,ArH),5.85(s,4H,ArH),6.20(s,4H,ArH); 13 C NMR (125MHz, CDCl 3 ,298K)δ:17.6(-CH 3 ),17.7(-CH 3 ),20.5(-CH 3 ),20.9(-CH 3 ),56.0(-OCH 3 ),60.1(-OCH 3 ),104.5,114.1(pyrrC),115.2(pyrrC),117.7(pyrrC),121.9(pyrrC),122.2(pyrrC),125.8,127.7,127.9,132.3,133.5,134.6,135.5(pyrrC),136.8,137.3, 139.1, 148.0, 148.1, 148.4, 151.1, 156.9, 167.7, 176.1; UV-vis (C...

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Abstract

The invention discloses a pyridine fused norcorrole compound and a preparation method thereof. The pyridine fused norcorrole compound has a structural formula as shown in formula (1). The preparation method mainly comprises the following steps: weighing a certain amount of amido norcorrole and aromatic aldehyde, putting into a reactor, adding newly steamed toluene solution to the reactor, stirring at 110 DEG C for 5-8 h, and tracking the reaction by a chromatographic method; cooling to room temperature after the reaction is completed, separating directly with a chromatography column, eluting with methylene chloride and normal hexane as eluents, collecting second brown color product as a crude product, and concentrating and drying the crude product to obtain the compound. The pyridine fused norcorrole compound and the preparation method thereof have the following advantages: the reaction conditions are stable, the yield is high, the operation is simple and safe, and batch production can be realized.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a pyridine-fused norcarbrole compound and a preparation method thereof. Background technique [0002] Norcorrole is a class of ring-contracted porphyrins, which lack two meso-position carbon atoms compared with conventional porphyrins. Because of the 16 π electrons on the conjugated ring, it exhibits obvious antiaromaticity, and its compact ring center has a large ring tension; nevertheless, it is still stable at room temperature and in air. However, due to the change in the structure of the porphyrin macrocycle, it has many novel properties, and has very broad application prospects in the fields of chemical catalysis, chemical material components, sensors, bio-related metal chemistry, and coordination chemistry. Carrying out derivatization research to provide functionalized molecules for scientific research has become one of the hot research issues at home...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D471/22
CPCC07D471/22
Inventor 李筱芳蒙燕葵于贤勇邓克勤
Owner HUNAN UNIV OF SCI & TECH
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