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Method for high-selectivity chemical synthesis of azetidine-condensed spiro-hexadienone

A chemical synthesis and high-selectivity technology, applied in organic chemistry and other fields, can solve problems such as complex structure, harsh reaction conditions, and functional group compatibility, and achieve high product yield, mild reaction conditions, and high selectivity.

Pending Publication Date: 2020-09-04
QUJING NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

It is worth noting that the former usually requires expensive transition metal catalysts, organic ligands with complex structures, and complex catalytic systems, and the reaction conditions are usually harsh; the latter usually requires the use of oxidants, so the compatibility of functional groups in the reaction is challenging. limit its further application

Method used

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  • Method for high-selectivity chemical synthesis of azetidine-condensed spiro-hexadienone

Examples

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Comparison scheme
Effect test

Embodiment 1

[0010] Example 1 A method for highly selective chemical synthesis of azetidine-fused spirocyclohexadienone.

[0011] With quinone imine monoketal 1a (R 1 = H, R 2 = 4-Me-C 6 h 4 ) (0.001 mol, 0.307 g) and allenyl ester 2 (0.0011 mol, 0.208 g) as starting materials, which were dissolved in 5 mL of toluene and cesium carbonate (Cs 2 CO 3 ) (0.0002mol, 0.065g) after moving to 80 o C reaction, wait for the reaction of quinone imine monoketal 1 to complete (t = 8 hours). Then the solvent was drained and the crude product was separated by column chromatography with eluent gradient elution to obtain the azetidine-fused spirocyclohexadienone derivative 3a.

Embodiment 2

[0012] Example 2 A method for chemically synthesizing azetidine-fused spirohexadienone with high selectivity.

[0013] With quinone imine monoketal 1b (R 1 = 2-Me, R 2 = 4-Me-C 6 h 4 ) (0.001 mol, 0.321 g) and allenyl ester 2 (0.0011 mol, 0.208 g) as starting materials, which were dissolved in 5 mL of toluene and cesium carbonate (Cs 2 CO 3 ) (0.0002mol, 0.065g) after moving to 80 o C reaction, wait for the reaction of quinoneimine monoketal 1 to complete (t = 4 hours). Then the solvent was drained and the crude product was separated by column chromatography with eluent gradient elution to obtain the azetidine-fused spirocyclohexadienone derivative 3b.

Embodiment 3

[0014] Example 3 A method for chemically synthesizing azetidine-fused spirocyclohexadienone with high selectivity.

[0015] With quinone imine monoketal 1c (R 1 = H, R 2 = 4-Ph-C 6 h 4 ) (0.001 mol, 0.369 g) and allenyl ester 2 (0.0011 mol, 0.208 g) were dissolved in 5 mL of toluene and cesium carbonate (Cs 2 CO 3 ) (0.0002mol, 0.065g) after moving to 80 o C reaction, wait for the reaction of quinone imine monoketal 1 to complete (t = 6 hours). Then the solvent was drained and the crude product was separated by column chromatography with eluent gradient elution to obtain the azetidine-fused spirocyclohexadienone derivative 3c.

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Abstract

A method for high-selectivity chemical synthesis of azetidine-condensed spiro-hexadienone belongs to the technical field of organic synthesis. According to the method, quinoneimine monoketal (QIKs) and allene ester which are easy to obtain are used as initial reaction raw materials, toluene is used as a reaction medium, cesium carbonate (Cs2CO3) is used as a catalyst, quinoneimine monoketal and allene ester are subjected to aza-Morta-Baylis-Hilman (aza-MBH) [2+2] cyclization / demethoxylation cascade reaction at 80 DEG C to synthesize a series of azetidine-condensed spiro cyclohexenone derivatives with novel structures. The method has the advantages that the raw materials are cheap and easy to obtain, the reaction can be amplified to gram-level reaction, any expensive transition metal catalyst and other complex reaction conditions are not needed in the reaction, and environmental pollution caused by heavy metal is avoided.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, in particular to a method for chemically synthesizing azetidine-fused spirocyclohexadienone with high selectivity. Background technique [0002] Azaspirocyclohexadienones are an extremely important class of organic functional molecules, which widely exist in natural products and drug molecules. Moreover, azaspirocyclohexadienone derivatives are often used as key intermediates in organic synthesis to synthesize important natural products and active molecules. The development of new methods to construct azaspirocyclohexadienone derivatives has important academic significance and application value. [0003] In recent years, there have been some reports in the literature on the construction of azaspirocyclohexadienone derivatives. In the synthetic method of constructing azaspirocyclohexadienone derivatives, it is an effective method to use transition metal combined with organic ligands to...

Claims

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Application Information

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IPC IPC(8): C07D205/12
CPCC07D205/12
Inventor 刘腾李永勤汪帆
Owner QUJING NORMAL UNIV