Free radical cyclization reaction method of 1,6-eneyne compound and ketone compound

A technology of ketone compounds and compounds, applied in the field of free radical bicyclization reaction, can solve problems such as limiting the construction of polycyclic compounds, and achieve a wide range of effects

Active Publication Date: 2019-12-06
NINGBO UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The previous cyclization reaction methods of olefin derivatives and ketones usually required the use of catalysts and / or bases, and only one cyclization of ketones α-C(sp 3 )-H bond oxidation reaction, which limits the construction of polycyclic compounds

Method used

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  • Free radical cyclization reaction method of 1,6-eneyne compound and ketone compound
  • Free radical cyclization reaction method of 1,6-eneyne compound and ketone compound
  • Free radical cyclization reaction method of 1,6-eneyne compound and ketone compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0031]

[0032] In the Schlenk bottle, add 1,6-enyne compound (39.8mg, 0.2mmol) shown in formula 1a, acetone (0.5mL), potassium persulfate compound salt (Oxone, 245.6mg, 0.4mmol), then react The reaction was stirred in an air atmosphere at 90°C, and the reaction process was monitored by TLC until the raw materials disappeared (reaction time was 16 hours). After the reaction was completed, the reaction solution was concentrated under reduced pressure to remove the solvent, and the residue was separated by column chromatography ( Elution solvent: ethyl acetate / n-hexane) to obtain the target product I-1 (82% yield, d.r.>20:1); 1 H NMR (500MHz, CDCl 3)δ: 7.68(d, J=8.0Hz, 2H), 7.38(t, J=8.0Hz, 2H), 7.16(t, J=7.5Hz, 1H), 4.08-4.05(m, 1H), 3.50- 3.48(m, 1H), 2.97-2.91(m, 1H), 2.57-2.51(m, 2H), 2.38-2.31(m, 1H), 2.17(s, 3H), 1.80-1.70(m, 2H), 1.36(s, 3H); 13 CNMR (125MHz, CDCl 3 )δ: 209.2, 178.0, 139.4, 128.9, 124.7, 119.8, 54.6, 52.9, 51.4, 41.1, 40.8, 36.6, 29.3, 22.5; HRMS m...

Embodiment 2

[0034] No oxidizing agent was added, other conditions were the same as in Example 1, and the yield of the target product I-1 was 0%.

Embodiment 3

[0036] Potassium persulfate (K 2 S 2 o 8 , 107.6mg, 0.4mmol) instead of potassium persulfate compound salt, all the other conditions are the same as in Example 1, and the yield of the target product I-1 is 41%.

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Abstract

The invention relates to a method for implementing a double cyclization reaction of a 1,6-eneyne compound and a ketone compound by two-time ketone alpha-C(sp<3>)-H bond oxidation in a catalyst-free and alkali-free system. The method includes adding the 1,6-eneyne compound, the ketone compound and an oxidant into a Schlenk reaction flask, and stirring for reaction under a certain temperature and air atmosphere conditions to obtain a double cyclization product.

Description

technical field [0001] The application belongs to the field of organic synthesis, and specifically relates to a free radical double-cyclization reaction method of 1,6-enynes and ketones in a catalyst-free and alkali-free system. Background technique [0002] Ketones are widely used as reaction solvents and synthons in organic chemistry due to their low cost and easy availability. Ketones α-C(sp 3 )-H bond oxidation strategy is an important way for it to participate in the construction of organic compounds as a synthon. In recent years, chemists have developed functionalization reactions of ketones with derivatives of alkenes, alkynes, amines, and heteroarynes. Among them, the reaction of ketone compounds and olefin derivatives has attracted much attention. On the one hand, it is simple and efficient and can simultaneously construct a variety of chemical bonds. On the other hand, this reaction enables the preparation of complex cyclic compounds with high atom economy. [...

Claims

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Application Information

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IPC IPC(8): C07D209/52C07D209/96
CPCC07D209/52C07D209/96
Inventor 魏文廷曹婷婷孟亚楠宋思哲
Owner NINGBO UNIV
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