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Synthesis of asymmetric dipyridyl substituted urea derivatives

A symmetrical dipyridyl and synthetic method technology, which is applied in the field of synthesizing unsymmetrical dipyridyl substituted urea derivatives, selenium or selenium dioxide catalytic carbonylation, can solve the problem of phosgene being highly toxic, corrosive to equipment, and easy to pollute the environment and other problems, to achieve the effect of easy clean production, mild reaction conditions, and less investment in equipment

Inactive Publication Date: 2004-07-07
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, the conventional method for synthesizing pyridine urea derivatives mainly adopts phosgene or phosgene-like isocyanate method. The disadvantage is that phosgene is highly toxic, and a large amount of corrosive chlorine-containing by-products are produced in the reaction process, which not only severely corrodes The equipment is also easy to pollute the environment
Moreover, the conventional method for synthesizing pyridine urea derivatives mainly adopts a three-step method, which is obviously cumbersome to operate and the overall yield is not too high.
Document [Tetrahedron Lett, 1999, 40(26), 4845~4846; CN01103688.5; CN01134394.X; CN02109056.5] reported the preparation method of asymmetric substituted urea, but it was not used to prepare asymmetric dipyridyl substituted Urea Derivatives

Method used

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  • Synthesis of asymmetric dipyridyl substituted urea derivatives
  • Synthesis of asymmetric dipyridyl substituted urea derivatives
  • Synthesis of asymmetric dipyridyl substituted urea derivatives

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Example 1 Synthesis of 1-(2-pyridyl)-3-(6-methoxy-3-pyridyl)urea under selenium catalysis

[0029] Add 2-methoxy-5-nitropyridine (10mmol), selenium (0.5mmol), 2-aminopyridine (10mmol), triethylamine (10mmol) and toluene 10ml into a 100ml stainless steel autoclave, replace with CO After three times, raise the CO pressure to 3.0MPa, put it in an oil bath at 130°C and stir for 4 hours, cool to room temperature, filter the reaction product, and purify the filtered crystals by column chromatography, the eluent is petroleum ether : Ethyl acetate (1:1), the eluate was concentrated to obtain the product, m.p.178~180°C, the yield was 74.5%.

Embodiment 2

[0030] Example 2 Synthesis of unsymmetrical dipyridyl substituted urea derivatives under selenium catalysis

[0031] Embodiment is summarized as follows in tabular form: (its reaction condition and step are with embodiment 1)

[0032]

[0033] Table 1: Selenium-catalyzed carbonylation of 2-methoxy-5-nitropyridine with aminopyridine derivatives

[0034] Reactive Synthesis of Unsymmetrical Bipyridine Urea Derivatives

[0035] sequence

[0036] Melting point Yield

[0037] Substrate Product

[0038] No

[0039] (°C) (%)

[0040]

Embodiment 3

[0041] Example 3 Synthesis of 1-(2-pyridyl)-3-(6-methoxy-3-pyridyl)urea catalyzed by selenium dioxide

[0042] Add 2-methoxy-5-nitropyridine (10mmol), selenium dioxide (0.5mmol), 2-aminopyridine (10mmol), triethylamine (10mmol) and toluene 10ml in the stainless steel autoclave of 100ml, use After CO replacement for three times, raise the pressure of CO to 3.0 MPa, put it in an oil bath at 130°C and stir for 4 hours, cool to room temperature, filter the reaction product, and purify the filtered crystals by column chromatography. The eluent is Petroleum ether: ethyl acetate (1:1), the eluate was concentrated to obtain the product, m.p.178-180°C, the yield was 77.1%.

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Abstract

A process for synthesizing the unsymmetrical dipyridinyl substituted urea derivative features the reaction between aminopyridine derivative, nitropyridine derivative, Se or SeO2 as catalyst, and triethylamine as cocatalyst in organic solvent at 50-200 deg.C in a sealed high-pressure reactor for 2-20 hr. Its advantages are simple process and high output rate.

Description

technical field [0001] The invention relates to a synthesis method of unsymmetrical dipyridyl substituted urea derivatives, in particular to a selenium or selenium dioxide catalyzed carbonylation method for synthesizing unsymmetrical dipyridyl substituted urea derivatives. technical background [0002] Pyridine urea derivatives containing peptide bonds (-CONH-) have certain biological and physiological activities. For example, N-benzoyl-N'-pyridyl urea derivatives are a class of high-efficiency insecticides [Documents: US4,405,552; EP8,880; DE3,126,263; US4,264,605; JP62,155,260; JP55,011,537; CA1,131,232, etc.]; N-phenyl-N'-pyridyl urea derivatives are an important class of herbicides and plant growth regulators [Document: EP401,168; US438,054; Plant Physiology Communication, 1989, ( 1), 17~19, etc.]; N-phenyl-N'-nitrogenated pyridyl urea derivatives are also a class of efficient plant growth regulators [Documents: US4,787,931; WO8,702,665; WO8,403,884 Wait】. In conventi...

Claims

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Application Information

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IPC IPC(8): C07D401/12
Inventor 陈金铸凌冈陆世维
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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