Method for preparing alpha-arylcarbonyl compound and product

A technology of aryl carbonyl and compound, which is applied in the field of organic chemical synthesis, can solve the problems of moisture sensitivity and special substrate, and achieve the effect of cheap and easy-to-obtain raw materials

Active Publication Date: 2021-07-20
ZHEJIANG NORMAL UNIVERSITY
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, the substrate of this type of method is special, and the reaction is very sensitive to moisture

Method used

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  • Method for preparing alpha-arylcarbonyl compound and product
  • Method for preparing alpha-arylcarbonyl compound and product
  • Method for preparing alpha-arylcarbonyl compound and product

Examples

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preparation example Construction

[0041] The specific implementation examples of the new method for preparing α-arylcarbonyl compounds provided by the present invention are introduced below, and multiple specific implementation examples are provided. It should be noted that the implementation of the present invention is not limited to the following implementation examples.

[0042] Example R 1Substitute the iodobenzene diacetate raw material to adopt the commercially available product, R 2 The substituted oxazoline part comes from commercially available products, and the preparation method of some compounds is as follows:

[0043]

[0044] 2-pentyl-4,5-dihydrooxazole (4a):

[0045] At 0°C, to 2-chloroethylammonia hydrochloride (10.21g, 88mmol) and Et 3 To a solution of N (28 mL, 200 mmol) in DCM (267 mL) was added hexanoyl chloride (11.2 mL, 80 mmol) dropwise. The system solution was warmed up to room temperature and stirred for 3h. The system solution was quenched with water, extracted with DCM, Na 2...

Embodiment 1

[0058] R 1 Take H, R 2 Taking the n-butyl group, according to the above method, 212.8 mg of yellow liquid compound 1 was obtained, and the yield was 62%.

[0059] 1 H NMR (600MHz, CDCl 3 ):δ7.83(d, J=7.9Hz, 1H), 7.38–7.34(m, 1H), 7.30(t, J=7.5Hz, 1H), 6.95–6.88(m, 1H), 4.26–4.19( m,1H),4.19–4.13(m,1H),4.01(t,J=7.5Hz,1H),3.85(t,J=9.5Hz,2H),2.07–1.97(m,1H),1.83–1.74 (m,1H),1.39–1.29(m,3H),1.25–1.18(m,1H),0.86(t,J=7.2Hz,3H).

[0060] 13 C NMR (151MHz, CDCl 3 ): δ169.1, 143.2, 139.7, 128.8, 128.7, 127.9, 101.8, 67.4, 54.4, 48.9, 34.0, 29.6, 22.7, 14.0.

[0061] IR(neat):2954,2929,2871,1659,1583,1561,1460,1435,1171,1108,732.

[0062] HRMS (ESI-TOF): calculated for [C 14 h 19 INO(M+H + )]:344.0506,found:344.0508.

Embodiment 2

[0064] R 1 Take H, R 2 Taking the isopentyl group, 225.0 mg of yellow liquid compound 2 can be obtained by the same method, and the yield is 63%.

[0065] 1 H NMR (600MHz, CDCl 3 ):δ7.86–7.82(m,1H),7.39–7.35(m,1H),7.33–7.29(m,1H),6.95–6.90(m,1H),4.26–4.14(m,2H),3.99 (t,J=7.5Hz,1H),3.90–3.80(m,2H),2.06–1.98(m,1H),1.84–1.76(m,1H),1.59–1.51(m,1H),1.32–1.23 (m,1H),1.14–1.06(m,1H),0.88–0.83(m,6H).

[0066] 13 C NMR (151MHz, CDCl 3 ): δ169.2, 143.3, 139.8, 128.8, 128.7, 128.0, 101.9, 67.5, 54.5, 49.2, 36.5, 32.2, 28.1, 22.7, 22.6.

[0067] IR(neat):2952,2901,2869,1660,1465,1435,1383,1365,1171,732.

[0068] HRMS (ESI-TOF): calculated for [C 15 h 21 INO(M+H + )]:358.0662,found:358.0662.

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Abstract

The invention discloses a method for preparing an alpha-aryl carbonyl compound, which comprises the following steps: activating an R1 substituted iodobenzene diacetate compound by Lewis acid, and then reacting with an R2 substituted oxazoline compound in the presence of alkali to obtain the alpha-aryl carbonyl compound, wherein R1 is selected from H, one or more alkyl groups, one or more halogenated alkyl groups, alkoxycarbonyl, halogen or multi-substitution formed by the combination of the above atoms, and R2 is selected from H, alkyl and substituted alkyl, wherein a substituent group is selected from cycloalkyl, halogen, alkoxy, heterocycloalkyl, substituted heterocycloalkyl, aryl, cyano, aryloxy and carbonyl. The method has the advantages of mild reaction conditions, easy product separation and simple operation.

Description

technical field [0001] The invention belongs to the field of organic chemical synthesis, in particular to a new method and product for preparing α-aryl carbonyl compounds. Background technique [0002] Due to the importance of α-arylcarbonyl compounds, they have been extensively studied. At present, it is an important intermediate in the synthesis of many active pharmaceutical molecules. α-Arylcarbonyl compounds are mainly used in the development of new drugs in the field of medicine. [0003] Compounds containing α-arylcarbonyl moieties have important pharmaceutical activity and physiological properties in the field of medicine. (J.Org.Chem.2001,66:3653; J.Med.Chem.1986,29:523; J.Am.Chem.Soc.1985,107:435; J.Am.Chem.Soc.1999,121 :2147.). [0004] So far, some synthetic methods of α-arylcarbonyl compounds have been reported successively. [0005] Cyclic ketones can react with diaryliodonium salts under the action of metal reagents to prepare α-aryl carbonyl compounds (Te...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D263/04C07D263/06C07D401/06C07C57/58
CPCC07D263/04C07D263/06C07D401/06C07C57/58
Inventor 李开笑詹亚玲李东阳罗凡田俊松彭勃
Owner ZHEJIANG NORMAL UNIVERSITY
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