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Preparation method of 3-acyl screw ring dibenzosuberenone compound

A kind of technology of acyl spirocyclic trienone and compound, which is applied in the field of preparation of 3-acyl spirocyclic trienone compound

Active Publication Date: 2018-05-22
HUNAN INSTITUTE OF SCIENCE AND TECHNOLOGY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] In order to enrich the synthesis method of 3-acyl spirotrienone compounds, the inventors, after painstaking research, proposed to use alkyne amides and acyl chlorides as raw materials to prepare 3-acyl spirotrienone compounds under photocatalytic conditions A new method, which has not been reported in the prior art

Method used

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  • Preparation method of 3-acyl screw ring dibenzosuberenone compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1-17

[0036] Embodiment 1-17 Reaction condition optimization:

[0037] Using alkyne amide and benzoyl chloride shown in formula three as raw materials, the influence of various conditions on the reaction (formula two) was explored, and representative examples were selected. The results are shown in table one:

[0038] Example

Reaction condition (variable)

Yield (%)

1

---

88

2

[Ru(bpy) 3 Cl 2 ] instead of [Ir(ppy) 3 ]

0

3

Eosin Y instead of [Ir(ppy) 3 ]

0

4

Do not join [Ir(ppy) 3 ]

0

5

in the dark

0

6

[Ir(ppy) 3 ] Feed amount is replaced by 5 mol %

89

7

36W fluorescent lamp replaces the LED lamp in Example 1

73

8

Na 2 CO 3 Instead of 2,6-lutidine

53

9

K 2 CO 3 Instead of 2,6-lutidine

47

10

Et 3 N instead of 2,6-lutidine

51

11

Toluene instead of CH 3 CN

32

12

BuOAc instead of CH 3 CN

61

...

Embodiment 18

[0046] Example 18 target product Synthesis

[0047] Add a magnetic stirring bar to the reactor, add the corresponding alkyne amide compound (0.2mmol) (refer to the reaction formula of formula 1 for the structure), photocatalyst [Ir(ppy) 3 ] (2mol%) and 2,6-lutidine (2.0 equivalents), then add benzoyl chloride (0.4mmol) and organic solvent acetonitrile (2mL), then replace the air in the reactor with argon to replace 3- After 5 times, the reactor was then placed in an oil bath equipped with magnetic stirring at a temperature of 100° C., and heated for 24 hours under the light condition of a 5W blue LED lamp as the light source. After the reaction was complete, the solvent was evaporated to dryness with a rotary evaporator, and the residue was separated and purified with a chromatographic column to obtain the target product with a yield of 83% ( 1 H NMR (400 MHz, CDCl 3 ): 7.84 (d, J = 7.6 Hz, 2H), 7.52(t, J = 8.0 Hz, 1H), 7.38 (t, J = 8.0 Hz, 2H), 7.23 (s, 5H), 7.22-7....

Embodiment 19

[0048] Example 19 target product Synthesis

[0049] Add a magnetic stirring bar to the reactor, add the corresponding alkyne amide compound (0.2mmol) (refer to the reaction formula of formula 1 for the structure), photocatalyst [Ir(ppy) 3 ] (2mol%) and 2,6-lutidine (2.0 equivalents), then add benzoyl chloride (0.4mmol) and organic solvent acetonitrile (2mL), then replace the air in the reactor with argon to replace 3- After 5 times, the reactor was then placed in an oil bath equipped with magnetic stirring at a temperature of 100° C., and heated for 24 hours under the light condition of a 5W blue LED lamp as the light source. After the reaction was complete, the solvent was evaporated to dryness with a rotary evaporator, and the residue was separated and purified with a chromatographic column to obtain the target product with a yield of 67% ( 1 H NMR (400 MHz, CDCl 3 ): 7.85 (t, J = 4.0 Hz, 2H), 7.54(d, J = 8.0 Hz, 1H), 7.41 (t, J = 8.0 Hz, 2H), 7.28-7.20 (m, 5H), 6....

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Abstract

The invention belongs to the field of pharmaceutical and organic intermediate synthesis, and concretely relates to a preparation method of 3-acyl screw ring dibenzosuberenone compound. An alkyne amidecompound as shown in a formula II and acyl chloride as shown in a formula III are reacted in an organic solvent under illumination with the existence of a photocatalyst [Ir(ppy)3] and alkali so as toobtain the 3-acyl screw ring dibenzosuberenone compound as shown in the formula I as the description.

Description

technical field [0001] The invention belongs to the field of medicine and organic intermediate synthesis, and in particular relates to a preparation method of a 3-acyl spirotrienone compound. Background technique [0002] The spirotrienone compound has a relatively unique structure, which makes it have many special properties. Compounds with spirotrienone structural fragments also widely exist in natural products, often as key structural skeletons with physiological activities and drug molecules ((1) CN104788360A; (2) European Journal of Medicinal Chemistry, 101(2015) 348-357). [0003] Due to the importance of functionalized spirotrienone compounds in chemical research and drug development, in recent years, the synthesis and application of spirotrienone compounds have gradually become a research hotspot in the field of organic and pharmaceutical chemistry. The attention of organic chemists, the synthetic method of this kind of functionalized spirotrienone compounds has als...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/54C07D409/06
CPCC07D209/54C07D409/06
Inventor 刘宇王巧林唐课文熊碧权张盼良
Owner HUNAN INSTITUTE OF SCIENCE AND TECHNOLOGY
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