Synthesis method of glycine derivatives

A technology of glycine derivatives, which is applied in the field of preparation of glycine derivatives, can solve the problems of heavy metal pollution, inability to use large-scale production, expensive catalysts, etc., achieve fast reaction speed, wide application range of substrates, and easy access to catalysts Effect

Inactive Publication Date: 2015-08-12
TONGJI UNIV
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Problems solved by technology

[0003]The many methods in the past mainly include Strecker, Ugi and Petais reactions ((a) Strecker, A. Ann. Chem. Pharm. 1850, 75, 27–45; (b) Ugi, I. Angew. Chem., Int. Ed. Engl. 1962, 1, 8–20; (c) Petasis, N. A.; Zavialov, I. A. J. Am. Chem. Soc. 1997, 119, 445–446.) and the use of photocatalysts to absorb energy to stimulate chemical reactions and the construction of carbon-carbon bonds in organic matter has attracted mor...

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  • Synthesis method of glycine derivatives
  • Synthesis method of glycine derivatives
  • Synthesis method of glycine derivatives

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Experimental program
Comparison scheme
Effect test

Embodiment 2

[0036] Reaction equation:

[0037]

[0038] where the Lewis acid is FeCl 2 , the solvent is acetonitrile, the catalyst EosinY,

[0039] Proceed as follows:

[0040] In a dry reaction tube, sequentially add 0.1mmol of glycine ester compound, 0.12mmol of indole, 0.005mmol of EosinY, FeCl 2 0.01 mmol.

[0041] Introduce oxygen at an atmospheric pressure, and irradiate with a blue LED for 40 hours. After the reaction, pass through a diatomaceous earth sand core, and remove the solvent under reduced pressure. The product is subjected to column chromatography to obtain the target product (petroleum ether / ethyl acetate = 40 / 1).

[0042] Yield 93%;

[0043]

[0044] 1 H NMR (400 MHz, CDCl 3) δ 8.19 (s, 1H), 7.82 (d, J = 7.8 Hz, 1H), 7.31 (d, J = 8.0 Hz, 1H), 7.20 (dd, J = 15.9, 8.5 Hz, 2H), 7.15 (s, 1H), 6.96 (d, J = 8.1 Hz, 2H), 6.56 (d, J = 8.2 Hz, 2H), 5.36 (s, 1H), 4.62 (s, 1H), 4.23 – 4.08 (m, 2H), 2.21 (s, 3H), 1.20 (t, J = 7.1 Hz, 3H). 13 C NMR (101 M...

Embodiment 3

[0047] Reaction equation:

[0048]

[0049] where the Lewis acid is FeCl 2 , the solvent is acetonitrile, the catalyst EosinY,

[0050] Proceed as follows:

[0051] In a dry reaction tube, sequentially add 0.1mmol of glycine ester compound, 0.12mmol of indole, 0.005mmol of EosinY, FeCl 2 0.01 mmol.

[0052] Introduce oxygen at an atmospheric pressure, and irradiate with a blue LED for 40 hours. After the reaction, pass through a diatomaceous earth sand core, and remove the solvent under reduced pressure. The product is subjected to column chromatography to obtain the target product (petroleum ether / ethyl acetate = 40 / 1).

[0053] Yield 89%;

[0054]

[0055] 1 H NMR (400 MHz, CDCl 3 ) δ 8.22 (s, 1H), 7.80 (d, J = 7.8 Hz, 1H), 7.33 (d, J = 8.0 Hz, 1H), 7.24 – 7.20 (m, 1H), 7.20 – 7.15 (m, 1H), 7.14 (s, 1H), 7.06 (d, J = 8.7 Hz, 2H), 6.52 (d, J = 8.8 Hz, 2H), 5.33 (s, 1H), 4.79 (s, 1H), 4.26 – 4.08 (m, 2H), 1.20 (t, J = 7.1 Hz, 3H). 13 C NMR (101 MHz, CD...

Embodiment 4

[0058] Reaction equation:

[0059]

[0060] where the Lewis acid is FeCl 2 , the solvent is acetonitrile, the catalyst EosinY,

[0061] Proceed as follows:

[0062] In a dry reaction tube, add glycine ester compound 0.1mmol, 5-nitroindole 0.12mmol, EosinY 0.005mmol, FeCl 2 0.01 mmol.

[0063] Introduce oxygen at an atmospheric pressure, and irradiate with a blue LED for 40 hours. After the reaction, pass through a diatomaceous earth sand core, and remove the solvent under reduced pressure. The product is subjected to column chromatography to obtain the target product (petroleum ether / ethyl acetate = 40 / 1).

[0064] Yield 90%;

[0065]

[0066] 1 H NMR (400 MHz, CDCl 3 ) δ 8.85 (s, 1H), 8.81 (s, 1H), 8.12 (d, J = 8.7 Hz, 1H), 7.42 – 7.32 (m, 2H), 7.15 (t, J = 7.4 Hz, 2H), 6.75 (t, J = 7.0 Hz, 1H), 6.63 (d, J = 7.7 Hz, 2H), 5.42 (s, 1H), 4.91 (s, 1H), 4.31 – 4.13 (m, 2H), 1.24 (t, J = 7.0 Hz, 3H). 13 C NMR (101 MHz, CDCl 3 ) δ 172.02 (s), 146.14 (s), 141...

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Abstract

The invention relates to a synthesis method of glycine derivatives. The synthesis method comprises that in an organic solvent, a glycinate compound and indole as raw materials and a Lewis acid additive undergo a reaction in the presence of dye EosinY as a catalyst at a normal temperature in O2 atmosphere under pressure of 1 atm for 40h, and the products are separated and purified. Compared with the prior art, the synthesis method solves problems of low reaction efficiency, high temperature requirements, high catalyst cost and heavy metal pollution, has the characteristics of high reaction yield, simple operation and environmental friendliness, and can be widely used in organic synthesis methodology and natural product synthesis.

Description

technical field [0001] The invention belongs to the technical field of organic chemical synthesis, and relates to a preparation method of glycine derivatives, which especially has the characteristics of high reaction yield, simple and convenient operation, and environmental protection. Background technique [0002] Glycine derivatives are a class of compounds with high biological activity. As an important fragment of many organic compounds, it is widely used in organic chemistry, medicine, pesticide, chemical industry and other fields. [0003] Many methods in the past mainly include Strecker, Ugi and Petais reactions ((a) Strecker, A. Ann. Chem. Pharm . 1850, 75, 27–45; (b) Ugi, I. Angew. Chem., Int. Ed. Engl . 1962, 1, 8–20; (c) Petasis, N. A.; Zavialov, I. A. J. Am. Chem. Soc . 1997, 119, 445–446.) and the use of photocatalysts to absorb energy for stimulating chemical reactions and the construction of carbon-carbon bonds in organic matter has attracted more and more...

Claims

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Application Information

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IPC IPC(8): C07D209/20C07D209/24
CPCC07D209/20C07D209/24
Inventor 陈余戈伟张荣华
Owner TONGJI UNIV
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