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A kind of furanone derivative and its synthetic method

A synthetic method and technology of furanone, which is applied in the field of iodine-catalyzed furanone derivatives and their synthesis, can solve the problems of difficult acquisition of raw materials, etc., and achieve the effects of cheap catalyst, environmental friendliness and convenient post-treatment

Inactive Publication Date: 2017-01-18
EAST CHINA NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

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

Method used

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  • A kind of furanone derivative and its synthetic method
  • A kind of furanone derivative and its synthetic method
  • A kind of furanone derivative and its synthetic method

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;

Embodiment 2

[0030] High resolution variable rate mass spectrometry data: HRMS (EI) calcd for C 19 h 14 INO 4 : 446.9968, found 446. Embodiment 2: trans-N-(4-iodo-2-oxo-5-phenylfuran-3-ylidene) methyl-4-methoxybenzamide synthesis

[0031]

[0032] N-amido-substituted enynyl esters, iodine, and solvents are selected respectively: trans-ethyl-2-(4,-methoxybenzamido)methylene-4-phenylbut-3-ynoic acid Ester, I 2 , toluene, the amount of raw materials is trans-ethyl-2-(4,-methoxybenzamido) methylene-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 67%, mp: 177-179°C.

[0033] NMR data: 1 H NMR (500MHz, CD 2 Cl 2 , Me 4 Si)δ3.89(s,3H),7.04(d,J=9.0Hz,2H),7.43-7.48(m,3H),7.96-8.04(m,5H),11.16(d,J=11.0Hz, 1H); 13 C NMR (125MHz, CD 2 Cl 2 , Me 4 Si)d 56.22, 60.80, 111.24, 114.97, 124.08, 127.57, 129.06, 129.08, 130.47, 130.62, 138.13, 149.21,...

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. ...

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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 Patents(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