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3-sulfonylation-indenone compound and preparation method thereof

A technology of indanone and sulfonylation is applied in the preparation of organic compounds, chemical instruments and methods, organic chemistry, etc., to achieve the effects of high yield, favorable for industrial production and mild reaction conditions

Active Publication Date: 2018-10-23
ZHENGZHOU UNIV
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Problems solved by technology

[0003] At present, the synthetic method of 3-sulfonylated-indanone compounds has not been reported, therefore, it is urgent to find a 3-sulfonylated-indanone with simple steps, mild reaction conditions, high regioselectivity and high yield The synthetic method of indanone compound

Method used

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  • 3-sulfonylation-indenone compound and preparation method thereof
  • 3-sulfonylation-indenone compound and preparation method thereof
  • 3-sulfonylation-indenone compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] The structural formula of 3-sulfonylated-indanone compound is as follows:

[0028]

[0029] The preparation steps are as follows:

[0030] Dissolve 2-(phenylethynyl)benzonitrile (0.2mmol) and p-toluenesulfonyl hydrazide (0.4mmol) in a mixed solution of 1.5mL acetone and 0.5mL water, then add cuprous iodide (0.04 mmol) and tert-butyl hydroperoxide (0.8 mmol), reacted at 45°C for 12 hours. After the reaction, it was extracted, dried, and the solvent was evaporated under reduced pressure, and the residue was separated by silica gel column chromatography (petroleum ether:ethyl acetate=10:1) to obtain a red solid.

[0031] Yield 72%. 1 H NMR (400MHz, CDCl 3 ,δ)7.98(d,J=7.6Hz,1H),7.58(d,J=7.2Hz,1H),7.56-7.47(m,3H),7.45-7.29(m,4H),7.29-7.19(m ,2H),7.14(d,J=8.1Hz,2H),2.35(s,3H); 13 C NMR (100MHz, CDCl 3 ,δ)194.3,151.3,145.2,141.22,139.9,136.8,135.0,130.4,129.6,129.5,128.8,127.9,127.8,127.6,124.4,123.9,21.6; HRMS Calcd for C 22 h 17 o 3 S[M+H] + :m / z 361.0898,Found:...

Embodiment 2

[0033] The structural formula of 3-sulfonylated-indanone compound is as follows:

[0034]

[0035] The preparation method is as follows:

[0036] Dissolve 5-methyl-2-(phenylethynyl)benzonitrile (0.2mmol) and p-toluenesulfonyl hydrazide (0.4mmol) in a mixed solution of 1.5mL acetonitrile and 0.5mL water, then add iodine Cuprous chloride (0.04mmol) and tert-butyl hydroperoxide (0.8mmol) were reacted at 80°C for 6 hours. After the reaction was completed, it was extracted, dried, and the solvent was evaporated under reduced pressure, and the residue was separated by silica gel column chromatography (petroleum ether:ethyl acetate=10:1) to obtain a yellow solid.

[0037] Yield: 65%. 1 H NMR (400MHz, CDCl 3 ,δ)7.83(d,J=7.6Hz,1H),7.53(d,J=8.0Hz,2H),7.41-7.33(m,4H),7.29-7.23(m,3H),7.13(d,J =8.0Hz,1H),2.36(s,3H),2.34(s,3H); 13 C NMR (100MHz, CDCl 3 ,δ) 194.6, 153.1, 151.5, 145.1, 140.0, 139.3, 138.4, 136.9, 135.0, 130.4, 129.6, 129.3, 129.1, 128.0, 127.8, 127.6, 125.4, 123.7, 2...

Embodiment 3

[0039] The structural formula of 3-sulfonylated-indanone compound is as follows:

[0040]

[0041] The preparation steps are as follows:

[0042] Dissolve 2-(p-tolylethynyl)benzonitrile (0.2mmol) and p-toluenesulfonyl hydrazide (0.4mmol) in a mixed solution of 1.5mL acetonitrile and 0.5mL water, then add cuprous iodide ( 0.04mmol) and tert-butyl hydroperoxide (0.8mmol), react at 60°C for 10 hours. After the reaction, it was extracted, dried, and the solvent was evaporated under reduced pressure, and the residue was separated by silica gel column chromatography (petroleum ether:ethyl acetate=10:1) to obtain a red solid.

[0043] Yield: 76%. 1 H NMR (400MHz, CDCl 3,δ)7.93(d,J=7.6Hz,1H),7.65-7.52(m,3H),7.50-7.46(m,1H),7.29(t,J=8.0Hz,1H),7.20-7.18(m ,4H),7.15(d,J=8.4Hz,2H),2.39(s,3H),2.34(s,3H); 13 C NMR (100MHz, CDCl 3 ,δ)194.5,150.5,145.2,141.3,140.2,139.8,137.0,135.0,130.5,129.6,129.3,128.8,128.4,127.8,124.9,124.3,123.7,21.6,21.5; HRMS Calcd for C 23 h 19 o 3 S[M+H]...

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Abstract

The invention discloses a 3-sulfonylation-indenone compound and a preparation method thereof. The preparation method is characterized in that the 3-sulfonylation-indenone compound is synthesized fromortho-aryne benzonitrile and aryl-sulfuryl hydrazine under the actions of copper iodide and tert-butyl hydroperoxide serving as catalysts. The 3-sulfonylation-indenone compound has the advantages of adoption of readily-available raw materials, mild reaction conditions, easiness and convenience in operation, high synthesis yield and contribution to industrial production. The derivative has potential application in the fields of chemical industry and medicine. A method is provided for the synthesis of the 3-sulfonylation-indenone compound for the first time.

Description

technical field [0001] The invention relates to the field of organic synthesis, in particular to a 3-sulfonylated-indanone compound and a preparation method thereof. Background technique [0002] Indanone and its derivatives have unique physical, chemical and biological activities, and widely exist in biologically active molecules such as natural products and drugs. The research on the synthesis methods and properties of indanone and its derivatives is still a field of chemistry, It is a research hotspot of common concern among pharmacy, physics and materials scientists (J. Med. Chem. 2007, 50, 4388-4404). In addition, sulfone compounds are important intermediate structures in organic synthesis, and exhibit a wide range of physical, chemical and biological activities in the fields of agriculture and medicinal chemistry (Chem. Commun. 2015, 51, 12111-12114, Tetrahedron Lett., 2017 ,58,487), therefore, it is of great practical significance to develop new synthetic methods for...

Claims

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Application Information

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IPC IPC(8): C07C315/00C07C317/24
CPCC07C315/00C07C317/24C07C2602/08
Inventor 陈晓岚孙凯於兵屈凌波孙远强
Owner ZHENGZHOU UNIV
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