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Furanone derivative and synthetic method thereof

A synthetic method and technology of furanone, which is applied in iodine-catalyzed furanone derivatives and its synthesis field, can solve the problems that raw materials are not easy to obtain, and achieve the effects of cheap catalyst, environmental friendliness and simple synthesis

Inactive Publication Date: 2015-08-12
EAST CHINA NORMAL UNIV
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  • Claims
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Problems solved by technology

However, the raw materials used in these methods are not easy to obtain

Method used

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  • Furanone derivative and synthetic method thereof
  • Furanone derivative and synthetic method thereof
  • Furanone derivative and synthetic method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0026] Example 1: trans-N-(4-iodo-5-(4 ， Synthesis of -methoxyphenyl)-2-oxofuran-3-ylidene)methylbenzamide

[0027]

[0028] N-amido-substituted enynyl esters, iodine, and solvents are selected respectively: trans-ethyl-2-(benzoylmethylene)-4-(4,-methoxyphenyl)but-3-ynoic acid Methyl ester, I 2 , toluene, the amount of raw materials is trans-ethyl-2-(benzoylmethylene)-4-(4,-methoxyphenyl) but-3-ynoic acid methyl ester 0.2mmol, iodine simple substance 0.4mmol, Toluene 2ml. Reacted at 100°C for 6 hours to obtain the target product, a yellow solid, with an isolated yield of 65%, mp: 215-216°C

[0029] NMR data: 1 H NMR (500MHz, CD 2 Cl 2 , Me 4 Si)δ3.85(s,3H),6.99(d,J=9.0Hz,2H),7.57(t,J=8.0Hz,2H),7.66(t,J=7.5Hz,1H),7.93-8.01 (m,5H),11.16(d,J=11.0Hz,1H); 13 C NMR (125MHz, CD 2 Cl 2 , Me 4 Si)d 55.99, 58.39, 112.17, 114.53, 121.42, 128.41, 129.31, 129.71, 132.13, 134.02, 136.53, 149.68, 161.65, 164.33, 168.58;

[0030] High resolution variable rate mass spectrometry...

Embodiment 3

[0035] Embodiment 3: Synthesis of trans-N-(4-iodo-2-oxo-5-phenylfuran-3-ylidene)methylbenzamide

[0036]

[0037] N-amido-substituted enynyl esters, iodine, and solvents are selected respectively: trans-ethyl-2-(benzoylmethylene)-4-phenylbut-3-ynoic acid methyl ester, I 2 , Toluene, the amount of raw materials is trans-ethyl-2-(benzoylmethylene)-4-phenylbut-3-ynoic acid methyl ester 0.2mmol, iodine simple substance 0.4mmol, toluene 2ml. React at 100°C for 6 hours to obtain the target product, a yellow solid, with an isolated yield of 64%, mp: 148-150°C.

[0038] NMR data: 1 H NMR (400MHz, CDCl 3 , Me 4 Si) δ7.41-7.46(m, 3H), 7.55(t, J=7.6Hz, 2H), 7.64(d, J=7.6Hz, 1H), 7.99-8.05(m, 5H), 11.23(d, J=11.2Hz,1H); 13 C NMR (100.6MHz, CDCl 3 , Me 4 Si)d 59.85, 111.59, 127.24, 128.15, 128.44, 128.67, 129.35, 130.24, 131.42, 133.81, 137.24, 149.30, 164.26, 168.39;

[0039] High-resolution mass spectrometry data: HRMS(EI)calcd for C 18 h 12 INO 3 :416.9862, found 416.9864. ...

Embodiment 4

[0040] Example 4: Synthesis of trans-N-(4-iodo-2-oxo-5-phenylfuran-3-ylidene)methyl pivalamide

[0041]

[0042] N-amido-substituted enynyl esters, iodine, and solvents are selected respectively: trans-ethyl-4-phenyl-2-(pivalylaminomethylene) but-3-ynoic acid methyl ester, I 2 , Toluene, the amount of raw materials is trans-ethyl-4-phenyl-2-(pivaloylaminomethylene) but-3-ynoic acid methyl ester 0.2mmol, iodine simple substance 0.4mmol, toluene 2ml. Reacted at 100°C for 6 hours to obtain the target product, a yellow liquid, with an isolated yield of 63%

[0043] NMR data: 1 H NMR (400MHz, CDCl 3 , Me 4 Si)δ1.35(s,9H),7.42-7.48(m,3H),7.82(d,J=11.2Hz,1H),8.02-8.04(m,2H),10.67(d,J=10.8Hz, 1H); 13 C NMR (100.6MHz, CDCl 3 , Me 4 Si)d 26.86, 39.43, 59.87, 110.95, 127.28, 128.60, 128.69, 130.19, 137.51, 149.14, 136.36, 177.00;

[0044] High-resolution mass spectrometry data: HRMS(EI)calcd for C 16 h 16 INO 3 :397.0175, found 397.0177.

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Abstract

The invention discloses a furanone derivative shown in a formula (I) and a synthetic method thereof. By taking an acylated amine substituted enyne ester compound as a raw material, under the action of a catalyst, the furanone derivative shown in the formula (I) is synthesized. The preparation method disclosed by the invention has the advantages of simple and easily available raw materials, simple and convenient post-treatment, cheap catalyst, good yield, environmental friendliness, and the like. The formula (I) is as shown in the specification.

Description

technical field [0001] The invention belongs to the technical field of organic compounds and synthesis, and relates to iodine-catalyzed furanone derivatives and a synthesis method thereof. Background technique [0002] Furanones are an important class of organic compounds, which widely exist in many natural and non-natural products, most of which have strong biological activity. It can be used as an intermediate in organic synthesis and has great value in drug synthesis. Because of these advantages of furanone, people are very enthusiastic about the synthetic research of furanone compound, so the method for synthesizing furanone is also more, for example multi-component reaction and enynoic acid compound can synthesize furanone such as: document (1 ) Xiao-Feng Wu, Haijun Jiao, Helfried Neumann, and Matthias Beller, Chem. Eur. J. 2012, 18, 16177 (2) Fabio Bellina, Matteo Biagetti, Adriano Carpita and Renzo Rossi Tetrahedron. 2001, 57. (3) Matteo Biagetti, Fabio Bellina, Adr...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/58
CPCC07D307/58
Inventor 李艳忠陶相华孙霞秦正晨孔令凯赵育磊郑重李艳丽周园园张芳芳
Owner EAST CHINA NORMAL UNIV
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