Synthetic method for pyrroline-3-formic ether compounds

A technology of ester compounds and dihydropyrrole, which is applied in the field of synthesis of dihydropyrrole-3-carboxylate compounds, can solve the problems of difficult availability of raw materials, atom economy, harsh reaction conditions, expensive catalysts, etc., to avoid intermediates Separation and purification process, easy operation, and the effect of reducing environmental burden

Inactive Publication Date: 2017-05-31
HENAN NORMAL UNIV
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  • Summary
  • Abstract
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  • Claims
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Problems solved by technology

Although these methods can effectively synthesize dihydropyrrole-3-carboxylates, there are still some problems that need to be solved urgently, such as: the catalyst used in the reaction is expensive, the reaction conditions are harsh, the raw materials are not easy to obtain, and the atom economy is low. Inadequacies also make the practicability of the above method greatly limited

Method used

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  • Synthetic method for pyrroline-3-formic ether compounds
  • Synthetic method for pyrroline-3-formic ether compounds
  • Synthetic method for pyrroline-3-formic ether compounds

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Effect test

Embodiment 1

[0015]

[0016] Add 1a (0.5 mmol, 81 mg) and acetonitrile (CH 3 CN, 5 mL), then 2a (5 mmol, 292 µL), palladium chloride (PdCl 2 , 0.05 mmol, 9 mg), copper acetate (Cu(OAc) 2 , 0.5 mmol, 91mg) and potassium iodide (KI, 0.5 mmol, 83 mg). In a CO / air (1 atm) atmosphere, stir the reaction at 80°C for 12 hours, then add 10 mL of saturated sodium chloride solution to quench the reaction, extract with ethyl acetate (10 mL × 3), combine the organic phases, and use water and sodium sulfate to dry. After filtration, spin-drying, and separation on a silica gel column (petroleum ether / ethyl acetate = 20:1), the yellow liquid product 3a (79 mg, 68%) was obtained. The characterization data of this compound are as follows: 1 H NMR (400 MHz, CDCl 3 ) δ 1.26 (t, J = 7.2Hz, 3H), 2.79 (t, J = 10.0 Hz, 2H), 3.37 (t, J = 10.4 Hz, 2H), 4.14 (q, J =7.2 Hz, 2H), 4.23 (s, 2H), 7.17 (s, 1H), 7.25-7.37 (m, 5H). 13 C NMR (100 MHz, CDCl 3 ) δ 14.7, 27.7, 54.0, 54.6, 58.9, 101.4, 127.1, 1...

Embodiment 2

[0018] According to the method described in Example 1, 1a (0.5 mmol, 81 mg) and acetonitrile (5 mL) were added to a 25 mL reaction vial, and then 2a (5 mmol, 292 µL), palladium acetate (0.05 mmol, 11 mg ) and copper acetate (0.5 mmol, 91mg). In a CO (1 atm) atmosphere, stir the reaction at 80°C for 12 hours, then add 10 mL of saturated sodium chloride solution to quench the reaction, extract with ethyl acetate (10 mL × 3), combine the organic phases, and wash with anhydrous sulfuric acid Sodium dry. After filtration, spin-drying, and silica gel column separation (petroleum ether / ethyl acetate = 20:1), the yellow liquid product 3a (47 mg, 41%) was obtained.

Embodiment 3

[0020] According to the method described in Example 1, 1a (0.5 mmol, 81 mg) and acetonitrile (5 mL) were added to a 25 mL reaction vial, and then 2a (5 mmol, 292 µL), tris(dibenzylideneacetone) Dipalladium (0.05 mmol, 46 mg) and copper acetate (0.5 mmol, 91 mg). In a CO (1 atm) atmosphere, stir the reaction at 80°C for 12 hours, then add 10 mL of saturated sodium chloride solution to quench the reaction, extract with ethyl acetate (10 mL × 3), combine the organic phases, and wash with anhydrous sulfuric acid Sodium dry. After filtration, spin-drying, and silica gel column separation (petroleum ether / ethyl acetate = 20:1), the yellow liquid product 3a (32 mg, 28%) was obtained.

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Abstract

The invention discloses a synthetic method for pyrroline-3-formic ether compounds, and belongs to the technical field of organic synthesis. The technical key point of the synthetic method is disclosed in the following diagram. Compared with the prior art, the synthetic method has the following advantages: (1) one-pot cascade reaction is adopted so as to avoid a complex intermediate separation and purification process, reduce waste emission and lower environment burdens; (2) raw materials can be easily obtained; (3) reaction is carried out below 100 DEG C, conditions are moderate, and operation is simple; (4) the applicable range of a substrate is wide; (5) the economy of reacting atoms is high.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a synthesis method of dihydropyrrole-3-carboxylate compounds. Background technique [0002] Dihydropyrrole-3-carboxylate compounds not only widely exist in natural products, but also have a wide range of applications in the fields of pesticides, industrial dyes, and biopharmaceuticals. At present, the synthesis methods of such compounds mainly include: 1) hydrogenation reduction of pyrrole-3-carboxylate compounds; 2) transition metal-catalyzed cascade reaction of aziridine and conjugated alkynoate; 3) substituted cyclopropane and Cascade reactions of primary amines, etc. Although these methods can effectively synthesize dihydropyrrole-3-carboxylates, there are still some problems that need to be solved urgently, such as: the catalyst used in the reaction is expensive, the reaction conditions are harsh, the raw materials are not easy to obtain, and the atom ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D207/277
CPCC07D207/277
Inventor 何艳王芳张新迎范学森
Owner HENAN NORMAL UNIV
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