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Synthesis method of alpha-diacetyloxymethyl substituted nitrogen-containing heterocyclic-ring compound

The technology of a diacetoxymethyl group and a synthetic method is applied in the field of organic synthesis in organic chemistry, can solve problems such as few reports on synthesis, and achieve the effects of wide application range, simple synthesis process, and cheap and easy-to-obtain raw materials

Active Publication Date: 2017-12-15
HENAN NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

It should be pointed out that although these two types of compounds have important research significance, their synthesis is rarely reported.

Method used

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  • Synthesis method of alpha-diacetyloxymethyl substituted nitrogen-containing heterocyclic-ring compound
  • Synthesis method of alpha-diacetyloxymethyl substituted nitrogen-containing heterocyclic-ring compound
  • Synthesis method of alpha-diacetyloxymethyl substituted nitrogen-containing heterocyclic-ring compound

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0013]

[0014] Add 1a (0.5mmol, 81mg), acetonitrile (5mL), copper acetate (0.5mmol, 90mg) and iodobenzenediacetic acid (0.5mmol, 161mg) to the 10mL Shrek tube successively, and vacuumize and fill with oxygen (1atm) It was placed in an 80°C oil bath and stirred for 12 hours. Then, 10 mL of saturated brine was added to quench the reaction, extracted with ethyl acetate (10 mL×3), and the organic phases were combined and dried over anhydrous sodium sulfate. Filtered, spin-dried, separated by silica gel column (petroleum ether / ethyl acetate=10 / 1) to obtain oily product 2a (89 mg, 64%). The characterization data of this compound are as follows: 1 H NMR (400MHz, CDCl 3 ):1.83-2.15(m,10H),3.09(dd,J 1 =16.8Hz,J 2 =9.2Hz, 1H), 3.43(t, J=8.8Hz, 1H), 3.96(dd, J 1 =8.0Hz,J 2 =4.8Hz, 1H), 6.64(t, J=7.2Hz, 1H), 6.72(d, J=8.4Hz, 2H), 6.81(d, J=4.8Hz, 1H), 7.16(t, J=8.4 Hz,2H). 13 C NMR (150MHz, CDCl 3 ):20.7,20.9,23.8,26.6,49.1,59.6,89.4,112.6,116.8,129.1,147.5,169.0. HRMS calcd ...

Embodiment 2

[0016] Add 1a (0.5mmol, 81mg), acetonitrile (5mL), copper acetate (0.25mmol, 45mg) and iodobenzenediacetic acid (0.5mmol, 161mg) to a 10mL Shrek tube in turn, and vacuumize and fill with oxygen (1atm). It was placed in an 80°C oil bath and stirred for 12 hours. Then, 10 mL of saturated brine was added to quench the reaction, extracted with ethyl acetate (10 mL×3), and the organic phases were combined and dried over anhydrous sodium sulfate. Filtered, spin-dried, separated by silica gel column (petroleum ether / ethyl acetate=10 / 1) to obtain oily product 2a (49 mg, 35%).

Embodiment 3

[0018] Add 1a (0.5mmol, 81mg), acetonitrile (5mL), copper acetate (1.0mmol, 180mg) and iodobenzenediacetic acid (0.5mmol, 161mg) to the 10mL Shrek tube successively, and vacuumize and fill with oxygen (1atm). It was placed in an 80°C oil bath and stirred for 12 hours. Then, 10 mL of saturated brine was added to quench the reaction, extracted with ethyl acetate (10 mL×3), and the organic phases were combined and dried over anhydrous sodium sulfate. Filtered, spin-dried, separated by silica gel column (petroleum ether / ethyl acetate=10 / 1) to obtain oily product 2a (67mg, 48%).

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Abstract

The invention discloses a synthesis method of an alpha-diacetyloxymethyl substituted nitrogen-containing heterocyclic-ring compound and belongs to the technical field of organic chemistry. An N-aryl substituted nitrogen-containing heterocyclic-ring compound 1 is dissolved in a solvent, copper acetate and iodobenzene diacetate are added, heating reaction is performed in the presence of oxygen, and the alpha-diacetyloxymethyl substituted nitrogen-containing heterocyclic-ring compound 2 is obtained after oxidization, ring contraction, oxalic acid esterification and other cascade reactions. The synthesis method has the advantages of being simple and convenient to operate, mild in condition, wide in substrate application range and the like and is suitable for industrial production.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis in organic chemistry, and specifically relates to a synthesis method of α-diacetoxymethyl-substituted nitrogen-containing heterocyclic compounds. Background technique [0002] Pyrrolidine and piperidine are very important nitrogen-containing heterocycles. They are not only the core structural units in many natural products and clinical drugs, but also important raw materials for the synthesis of various organic functional molecules such as spices, dyes, and biological probes. . On the other hand, methylene diacetate is one of the main protected forms of aldehyde carbonyl, which has the advantages of high generation efficiency, relatively stable under various reaction conditions, and easy removal. At the same time, methylene diacetate compounds are also commonly used intermediates in organic synthesis. As a hybrid of nitrogen-containing heterocycles and methylene diacetate, α-diacetoxym...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D207/08C07D211/22
CPCC07D207/08C07D211/22
Inventor 何艳张新迎王芳范学森
Owner HENAN NORMAL UNIV