Process for synthesizing multi-substituent pyridine derivative and dipyridine derivative from nitrile

A synthesis method and derivative technology, applied in silicon organic compounds, organic chemistry, etc., can solve the problems of difficult synthesis of multi-substituted pyridine derivatives, bipyridine derivatives, poor selectivity, low yield, etc., and achieve a scientific and reasonable synthesis method , product is easy, the effect of high yield

Inactive Publication Date: 2002-07-03
席振峰 +2
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  • Abstract
  • Description
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AI Technical Summary

Problems solved by technology

[0003] Although pyridine derivatives and bipyridine derivatives can be synthesized by traditional methods, the yield is low and the selectivity is poor
And it is difficult to synthesize multi-substituted pyridine derivatives and bipyridine derivatives by traditional synthetic methods

Method used

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Examples

Experimental program
Comparison scheme
Effect test

example 1

[0025] One of the I class compounds in the structural formula (R=nPr): 2-phenyl-3,4,5,6-tetra(n-propyl)-pyridine synthesis

[0026] Under the protection of an inert gas (such as high-purity nitrogen), add 1 mmol of 4,7-diiodo-5,6-di(n-propyl )-4,6-quinadiene and 5 mL of anhydrous and oxygen-free treated ether solvent. First, the above ether solution was lowered to a lower temperature (-78°C to -55°C) with a cold bath (such as a dry ice-acetone bath), and then 4 mmol tert-butyllithium (1.6M, n-pentane solution) was added dropwise under magnetic stirring. ). After the reaction was stirred at -78°C to -55°C for 1 hour, 2 mmol of hexamethylphosphoramide and 4 mmol of benzonitrile were added. The cooling bath was removed, and the reaction solution was gradually warmed to room temperature (20°C to 28°C), stirred for 1 hour, and then washed with about 1 mL of saturated NaHCO 3 Aqueous solution quenched the reaction. Extracted three times with petroleum ether (each 10mL). The ext...

example 2

[0028] The second compound of class I in the structural formula (R=nPr, R'=4-methoxyphenyl): 2-(4-methoxyphenyl)-3,4,5,6-tetra(n-propyl) - Synthesis of pyridine.

[0029] The synthetic route is basically the same as above. The starting material diiodide compound in this synthesis is 4,7-diiodo-5,6-di(n-propyl)-4,6-quinadiene, and the starting material nitrile is 4-methoxybenzonitrile. Obtained 0.319 g of pure product (purity>98%, yellow liquid). Isolated yield 80%. The NMR and high-resolution mass spectrometry data of the compound are as follows. 1 H NMR (CDCl 3 , Me 4 Si) δ0.79(t, J=7.2Hz, 3H), 0.98(t, J=7.2Hz, 3H), 1.03-1.13(m, 6H), 1.32-1.44(m, 2H), 1.49-1.62( m, 4H), 1.67-1.80(m, 2H), 2.44-2.54(m, 2H), 2.54-2.68(m, 4H), 2.68-2.79(m, 2H), 3.82(s, 3H), 6.92( d, J=8.4Hz, 2H), 7.32(d, J=8.4Hz, 2H). 13 C NMR (CDCl 3 , Me 4 Si)δ14.42(CH 3 ), 14.59 (CH 3 ), 14.89 (CH 3 ), 15.01 (CH 3 ), 23.63 (CH 2 ), 24.54 (CH 2 ), 24.59 (CH 2 ), 31.00 (CH 2 ), 31.47 (CH 2 ), ...

example 3

[0031] The third compound of class I in the structural formula (R=Et, R'=4-methylphenyl): the synthesis of 2-(4-methylphenyl)-3,4,5,6-tetraethyl-pyridine.

[0032] The synthetic route is basically the same as above. The starting raw material diiodide compound of this synthesis is 3,6-diiodo-4,5-diethyl-3,5-octadiene, and the starting raw material nitrile is 4-methylbenzonitrile. 0.163 g of pure product was obtained (purity>98%, yellow liquid). Isolated yield 58%. The NMR and high-resolution mass spectrometry data of the compound are as follows. 1 H NMR (CDCl 3 , Me 4 Si)δ 1.00(t, J=7.5Hz, 3H), 1.16-1.32(m, 9H). 2.38(s, 3H), 2.58(m, 2H), 2.64-2.77(m, 4H), 2.82(m , 2H), 7.19(d, J=7.8Hz, 2H), 7.29(d, J=7.8Hz, 2H). 13 C NMR (CDCl 3 , Me 4 Si)δ14.64(CH 3 ), 15.35 (CH 3 ), 15.43 (CH 3 ), 15.63 (CH 3 ), 21.25 (CH 3 ), 21.42 (CH 2 ), 21.77 (CH 2 ), 22.03 (CH 2 ), 28.33 (CH 2 ), 128.66(2CH), 128.74(2CH), 132.47(C), 133.17(C), 136.72(C), 139.53(C), 149.21(C), 156.67(C),...

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Abstract

A process for synthesizing multi-substituent pyridine derivative and dipyridine derivative directly from nitrile and organolithium compound includes reaction of the 1,4-diiodo-1,3-butadiene derivative dissolved in ether or tetrahydrofuran solvent on n-butyl lithium or tert-butyl lithium at low-temp, adding nitrile and hexamethyl phosphamide, heating, quenching reaction, extracting, washing, drying, concentrating and purifying. Its advantages include high output rate and easy purifying of product.

Description

technical field [0001] The field of the present invention is the synthesis of organic synthesis intermediates, especially the synthesis method of polysubstituted pyridine derivatives and bipyridine derivatives. Background technique [0002] Pyridine derivatives are an important class of organic compounds, which are the basic building blocks of many natural medicines, pesticides, dyes, vitamins and various alkaloids. Pyridine derivatives and bipyridine derivatives play an important role in chemical biology and many interdisciplinary subjects. For example, as ligands of metal-organic compounds, they play an important role in coordination chemistry, polymer materials science, and metal-organic chemistry. [0003] Although pyridine derivatives and bipyridine derivatives can be synthesized by traditional methods, the yield is low and the selectivity is poor. And it is difficult to synthesize multi-substituted pyridine derivatives and bipyridine derivatives by traditional synthe...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/09C07D401/04C07F7/08
Inventor 席振峰陈敬龙宋秋玲
Owner 席振峰
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