Oxa-spiro bridged UPy compound and synthesis method thereof

A technology of ureido pyrimidinone and bis-ureido pyrimidinone is applied in the field of synthesis technology of oxa spiro ring bridged ureido pyrimidinone compound, can solve the problems of lack of dynamic reversibility, poor degradability and the like, and achieves good application prospects , mild reaction conditions, good mechanical properties

Active Publication Date: 2018-11-02
CHANGZHOU UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, such traditional polymers obtained by covalent bonds have poor degradability, no dynamic reversibility, and no stimuli responsiveness.

Method used

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  • Oxa-spiro bridged UPy compound and synthesis method thereof
  • Oxa-spiro bridged UPy compound and synthesis method thereof
  • Oxa-spiro bridged UPy compound and synthesis method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031] Synthesis of step 1, oxaspiro dinitro compound (compound A):

[0032] Add 5.00 g of o-nitrobenzaldehyde, 2.25 g of pentaerythritol and 0.30 g of catalyst p-toluenesulfonic acid into a 250 mL three-necked flask, then add 40 mL of toluene as a solvent, and set up a water separator to remove water in the reaction. Maintain 140°C, stir the reaction, reflux for 3h, and stop heating. Continue to reflux until the temperature of the reaction system drops to room temperature and stop. Rotary evaporation, remove toluene, with saturated NaHCO 3 The solution was washed (50mL×2), and then washed with distilled water (50mL×2), and the crude product was obtained by suction filtration. Finally, with CH 3 OH / CH 2 Cl 2 After recrystallization, suction filtration and drying at 50° C. for 3 h under vacuum, the product is a brown powdery solid with a yield of 98.80%.

[0033] Step 2, the synthesis of oxaspiro diamino compound (compound B):

[0034] Add 6.00 g of compound A and 0.40 g...

Embodiment 2～6

[0041] The synthesis of Compound A, Compound B and Compound C is the same as in Example 1, and the synthesis of Compound D is synthesized with reference to step 4 of Example 1, only changing Compound B: The molar ratio of Compound C is 1:2.0, 1:2.1, 1: 2.3, 1:2.4, 1:2.5, the target product is obtained.

Embodiment 7

[0043] Step 1, the synthesis of compound A was synthesized with reference to Example 1.

[0044] Step 2, the synthesis of compound B was synthesized with reference to Example 1.

[0045] Synthesis of step 3, activated ureidopyrimidinone compound (compound C):

[0046] Add 0.79g of 6-isoheptylisopyrimidine and 1.14g of N,N'-carbonyldiimidazole (CDI) into a 50mL three-necked flask, and exhaust the oxygen and moisture. Under nitrogen protection, add CHCl after washing with water for 15 times and drying 3 20mL, stirred at room temperature for 6h, and stopped the reaction. Wash with water (30 mL×2) and saturated brine (30 mL×2) successively, collect the organic phase, dry over anhydrous magnesium sulfate, and filter.

[0047] Step 4, the synthesis of compound D was synthesized with reference to Example 1.

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Abstract

The invention relates to a compound and a synthesis method thereof, in particular to an oxa-spiro bridged UPy compound and a synthesis method thereof. The oxa-spiro bridged UPy compound is an oxa-spiro bridged UPy compound condensed on basis of pentaerythritol. The synthesis method comprises the steps as follows: an oxa-spiro binitro compound is synthesized firstly, an oxa-spiro biamino compound is synthesized, then, an activated UPy compound is synthesized, and finally, the oxa-spiro bridged UPy compound based on pentaerythritol is synthesized. The method is simple in process and has wide application prospects, and raw materials are easy to obtain. Resources can be saved and the total yield can be increased. A dynamically reversible super-molecular polymer structure with good mechanical performance is formed.

Description

technical field [0001] The invention belongs to the field of synthesis of supramolecular polymer materials, and in particular relates to a synthesis process of an oxaspiro ring bridged ureidopyrimidinone (UPy) compound. Background technique [0002] In the 1930s, oxaspiro compounds were first discovered in American saponin plants. With the development of organic chemistry, oxaspiro compounds have become more and more widely used, and can be used in catalysis to degrade drugs. Luminescent materials, used as antibacterial agents and applied in biosensing, etc. The pentaerythritol oxaspiro compound has strong rigidity, and is composed of two oxa six-membered rings connected by a spiro carbon atom, and the rings are in a staggered chair conformation. The oxygen atom on the six-membered ring has a lone pair of electrons, which is electronegative and may participate in coordination, so it is widely used. Recently, we (Dyes and Pigments 2018, 149, 921.) synthesized and characteri...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D493/10
CPCC07D493/10
Inventor 肖唐鑫赵伟孙小强
Owner CHANGZHOU UNIV
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