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Method for synthesizing cis/trans oxygen and nitrogen heteroatom-containing spiro compound

A technology of spiro compounds and heteroatoms, applied in the field of organic synthesis, can solve the problems of harsh reaction conditions, small expansion range of substrates, long reaction time, etc., and achieve the effects of high yield, environmental friendliness and simple operation.

Active Publication Date: 2020-10-30
YANGZHOU UNIV
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  • Description
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Problems solved by technology

[0005] Through the analysis of published literature, it can be seen that there are still some problems in the method of synthesizing pyridine spirocyclic derivatives, such as the raw materials used need to be prepared in advance, the reaction conditions are harsh, the reaction time is long, the substrate expansion range is small, etc., and cannot Synthesis of Spiral Compounds Containing Oxygen and Nitrogen Heteroatoms

Method used

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  • Method for synthesizing cis/trans oxygen and nitrogen heteroatom-containing spiro compound
  • Method for synthesizing cis/trans oxygen and nitrogen heteroatom-containing spiro compound
  • Method for synthesizing cis/trans oxygen and nitrogen heteroatom-containing spiro compound

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] To prepare cis-dimethyl-8,11-bis(4-methoxyphenyl)-7-((E)-4-methoxystyryl)-3,3-dimethyl -1,5-dioxa-2,4-dioxa-8-azaspiro[5.5]undec-9-ene-9,10-dicarboxylate as an example, its preparation method is as follows:

[0025]

[0026] Add 5 mL of dichloromethane and 0.1800 g (1.5 mmol) of anhydrous magnesium sulfate to a 10 mL Schenk tube, then add 0.2937 g (1.1 mmol) of (1E,2E)-N,3-bis(4-methoxyphenyl) Prop-2-ene-1-imine, 0.2096g (0.8mmol) 5-(4-methoxybenzylidene)-2,2-dimethyl-1,3-dioxane-4,6- Diketone, finally add 0.1420g (1mmol) butynedioic acid dimethyl ester, react at room temperature for 12 hours, remove anhydrous magnesium sulfate by suction filtration after the reaction finishes, evaporate and concentrate the filtrate, utilize a silica gel column to carry out column chromatography purification process, Pure cis-dimethyl-8,11-bis(4-methoxyphenyl)-7-((E)-4-methoxystyryl)-3,3-dimethyl- 1,5-Dioxa-2,4-dioxa-8-azaspiro[5.5]undec-9-ene-9,10-dicarboxylate, isolated in 63% yi...

Embodiment 2

[0029] To prepare trans-dimethyl-8,11-bis(4-methoxyphenyl)-7-((E)-4-methoxystyryl)-3,3-dimethyl -1,5-dioxa-2,4-dioxa-8-azaspiro[5.5]undec-9-ene-9,10-dicarboxylate as an example, its preparation method is as follows:

[0030]

[0031]Purification by column chromatography using a silica gel column in Example 1 to obtain pure trans-dimethyl-8,11-bis(4-methoxyphenyl)-7-((E)-4-methanol Oxystyryl)-3,3-dimethyl-1,5-dioxa-2,4-dioxa-8-azaspiro[5.5]undec-9-ene-9,10 -dicarboxylate, its isolated yield is 30%, and the structural characterization data are as follows:

[0032] 1 H NMR (400MHz, CDCl 3 )δ: 7.28(d, J=9.2Hz, 2H, ArH), 7.24(t, J=8.4Hz, 2H, ArH), 7.04(d, J=7.6Hz, 2H, ArH), 6.89(d, J =8.4Hz,2H,ArH),6.79(d,J=8.8Hz,2H,ArH),6.74(d,J=8.4Hz,2H,ArH),6.36(d,J=15.6Hz,1H,CH) ,5.74(dd,J 1 =16.0Hz,J 2 =9.2Hz,1H,CH), 4.77(d,J=8.8Hz,1H,CH),4.56(s,1H,CH),3.81(s,3H,OCH 3 ),3.75(s,6H,2OCH 3 ),3.55(s,3H,OCH 3 ),3.50(s,3H,OCH 3 ),1.72(s,3H,CH 3 ),1.52(s,3H,CH 3 ); 13 C NMR (100MHz, ...

Embodiment 3

[0034] To prepare cis-dimethyl-11-(4-methoxyphenyl)-7-((E)-4-methoxystyryl)-3,3-dimethyl-1 with the following structural formula, 5-dioxa-8-(p-tolyl)-2,4-dioxa-8-azaspiro[5.5]undec-9-ene-9,10-dicarboxylate as an example, its The preparation method is as follows:

[0035]

[0036] Add 5 mL of dichloromethane and 0.1203 g (1.0 mmol) of anhydrous magnesium sulfate to a 10 mL Schenk tube, then add 0.3012 g (1.2 mmol) of (1E,2E)-3-(4-methoxyphenyl)-N- (p-tolyl)prop-2-en-1-imine, 0.2620g (1.0mmol) 5-(4-methoxybenzylidene)-2,2-dimethyl-1,3-dioxane -4,6-diketone, finally add 0.1420g (1mmol) dimethyl butynedioate, react at room temperature for 12 hours, remove anhydrous magnesium sulfate by suction filtration after the reaction is completed, evaporate and concentrate the filtrate, and use a silica gel column for column Chromatographic purification treatment, you can get cis-dimethyl-11-(4-methoxyphenyl)-7-((E)-4-methoxystyryl)-3,3-dimethyl -1,5-dioxa-8-(p-tolyl)-2,4-dioxa-8-azasp...

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Abstract

The invention discloses a method for synthesizing a cis / trans [2,4-dioxa-8-azaspiro[5.5]undec-9-ene compound. According to the method, the cis / trans [2,4-dioxa-8-azaspiro[5.5]undec-9-ene compound is obtained through one-step reaction of a compound represented by a formula 1, a compound represented by a formula 2 and dimethyl butynedicarboxylate in the presence of anhydrous magnesium sulfate by taking dichloromethane as a solvent. The target molecule has important application value in the fields of medicine, pesticide, life science and the like. According to the method, the used raw materials are easy to obtain, a transition metal catalyst is not needed, the operation is simple and convenient, and an efficient, economical and applicable method is provided for synthesizing the cis / trans [2,4-dioxa-8-azaspiro[5.5]undec-9-ene compound.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and relates to a method for synthesizing cis / trans spiro compounds containing oxygen and nitrogen heteroatoms. Background technique [0002] Nitrogen-containing heterocyclic compounds usually have unique biological activity, low toxicity and high systemic property, and are often used as structural units of medicine and pesticide, and play an important role in the application of medicine and pesticide. The synthesis of derivatives of nitrogen-containing heterocyclic compounds has always been a research hotspot in the field of organic synthesis. Among them, nitrogen heterocyclic compounds containing pyridine rings have important medicinal value. Milrinone (1) can inhibit the phosphodiesterase of the heart, produce positive contraction and expansion of peripheral blood vessels, and is suitable for short-term treatment of patients with severe congestive heart failure who are ineffective in...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D491/113
CPCC07D491/113
Inventor 孙晶刘旦韩莹颜朝国
Owner YANGZHOU UNIV
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