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Method for compounding pyrroline derivative in one step by cyclizing and coupling suzuki

A technology for dihydropyrrole and derivatives, applied in chemical recovery, organic chemistry, etc., to achieve the effects of high yield, stable performance, and simple process

Inactive Publication Date: 2017-08-18
SHANDONG UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Although many chemical synthesis methods of pyrrole derivatives have been developed, the single-molecule cyclic pyrrole compound produced by one-step reaction with the end of a three-membered carboallyne has rarely been reported so far.

Method used

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  • Method for compounding pyrroline derivative in one step by cyclizing and coupling suzuki
  • Method for compounding pyrroline derivative in one step by cyclizing and coupling suzuki
  • Method for compounding pyrroline derivative in one step by cyclizing and coupling suzuki

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0052] 3-vinyl-4-p-methoxybenzyl-N-p-methylbenzenesulfonyl-2,3-dihydropyrrole:

[0053] figure 2 The chemical formula of embodiment 1

[0054] In a 25 mL test tube reactor, exchange the air with nitrogen 3 times. In a nitrogen atmosphere, the substrate 1a (0.03mmol, 10mg), 2a (0.07 mmol, 10.9 mg), PdCl 2 (PPh 3 ) 2 (0.003 mmol, 2.3 mg), K 3 PO 4 (0.06mmol, 13.6 mg), weighed in turn, added to the reaction tube, evacuated to replace nitrogen, and added ethylene glycol dimethyl ether and dioxane (1V:15V) (total 2 mL) under nitrogen atmosphere. The reaction system was heated to 50°C and reacted for 10 hours. After the reaction was detected by TLC, the system was cooled to room temperature. Silica gel was added directly, spin-dried and column chromatographed to obtain light yellow paste 3aa (97%). 1 H NMR (400 MHz, CDCl 3 , δ ppm): 7.66–7.61 (m, 2H), 7.35–7.31 (m, 2H), 6.97–6.94 (m,2H), 6.82–6.78 (m, 2H), 6.01 (q, J = 1.6 Hz, 1H), 5.26 (ddd, J = 16.9 Hz,10.0 Hz, 8....

Embodiment 2

[0056] image 3 The chemical formula of embodiment 2

[0057] In a 25 mL test tube reactor, exchange the air with nitrogen 3 times. In a nitrogen atmosphere, the substrate 1b (0.03mmol, 8.9mg), 2b (0.07 mmol, 10.9 mg), PdCl 2 (PPh 3 ) 2 (0.003 mmol, 2.3 mg), K 3 PO 4 (0.06mmol, 13.6 mg), weighed in turn, added to the reaction tube, evacuated to replace nitrogen, and added ethylene glycol dimethyl ether and dioxane (1V:15V) (total 2 mL) under nitrogen atmosphere. The reaction system was heated to 50°C and reacted for 10 hours. After the reaction was detected by TLC, the system was cooled to room temperature. Silica gel was added directly, spin-dried and column chromatographed to obtain light yellow paste 3bb (98%). 1 H NMR (400 MHz, CDCl 3 , δ ppm): 7.63–7.57 (m, 2H), 7.32 (d, J = 8.0 Hz, 2H), 7.00(td, J = 8.5 Hz, 6.5 Hz, 1H), 6.82–6.73 (m, 2H), 6.00 (q, J = 1.6 Hz, 1H),5.25 (ddd, J = 16.8 Hz, 10.1 Hz, 8.7 Hz, 1H), 4.98–4.88 (m, 2H), 3.67 (dd, J = 10.6 Hz, 9...

Embodiment 3

[0059] Figure 4 The chemical equation of embodiment 3

[0060] In a 25 mL test tube reactor, exchange the air with nitrogen 3 times. In a nitrogen atmosphere, the substrate 1c (0.2mmol, 74.5mg), 2c (0.5 mmol, 68.1 mg), PdCl 2 (PPh 3 ) 2 (0.02 mmol, 14 mg), K 3 PO 4 (0.4mmol, 84.9 mg), weighed in turn, added to the reaction tube, evacuated to replace nitrogen, and added ethylene glycol dimethyl ether and dioxane (1V:15V) (total 4 mL) under nitrogen atmosphere. The reaction system was heated to 50°C and reacted for 10 hours. After the reaction was detected by TLC, the system was cooled to room temperature. Directly add silica gel, spin dry column chromatography, obtain light yellow paste 3cc (93%). 1 H NMR (400 MHz, CDCl 3 , δ ppm): 7.66–7.61 (m, 2H), 7.33 (d, J = 8.0 Hz, 2H), 7.07(d, J = 7.8 Hz, 2H), 6.94 (d, J = 7.9 Hz, 2H), 6.03 (q, J = 1.6 Hz, 1H), 5.27(ddd, J = 16.9 Hz, 10.1 Hz, 8.9 Hz, 1H), 4.98–4.85 (m, 2H), 3.66 (dd, J =10.9 Hz, 9.8 Hz, 1H), 3.29...

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Abstract

The invention relates to a method for compounding a pyrroline derivative in one step by cyclizing and coupling suzuki and belongs to the field of chemical compounding of allene (1,2-propadiene) by cyclizing. The method is characterized in that (1) transition metal elements are adopted for catalyzing; (2) allene is used as a raw material for compounding; (3) the reaction is performed when the reaction temperature is low temperature or normal temperature; (4) the reaction is completed in one step; (5) the catalyst is fully recycled; (6) water is strictly removed from a reaction solvent and the trace level is achieved; (7) 2,3-pyrroline five-element ring is the main structure of the generated product; (8) the physical and chemical properties of the generated product are not changed under normal temperature and high temperature environments; (9) the yield of the generated product is more than or equal to 98 wt%; (10) the generated side products are easily removed according to a conventional method.

Description

technical field [0001] The method for synthesizing dihydropyrrole derivatives in one step through suzuki cyclization coupling belongs to the technical field of organic compound technology application. Background technique [0002] Pyrrole derivative monomer is an important class of five-membered nitrogen heterocyclic compounds. Molecular materials and other fields have a wide range of applications. At present, the research on the total synthesis of natural cyclic tetrapyrrole compounds is a hot spot in the field of organic chemistry. One of the very important links is the construction of various substituted pyrrole monomer synthons. The difficulty of obtaining these pyrrole monomer synthons It is often a key factor in determining whether the reaction route is reasonable. Although many chemical synthesis methods of pyrrole derivatives have been developed, there are few reports on the single-molecule cyclic pyrrole compound produced by the one-step reaction of the end of the...

Claims

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Application Information

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IPC IPC(8): C07D207/48C07D405/06
CPCY02P20/584C07D207/48C07D405/06
Inventor 刘会梁寒冰董旭朱玉花韩颖
Owner SHANDONG UNIV OF TECH
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