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One-step synthesis method of 2-acyl substituted isoindoline-1-one compounds

A technology of ketone compound and isoindoline is applied in the field of 2-acyl substituted isoindoline, which can solve the problems of harsh reaction conditions and the use of precious metals, and achieve simple operation and environmental friendliness

Inactive Publication Date: 2016-08-17
SHAANXI NORMAL UNIV
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  • Abstract
  • Description
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AI Technical Summary

Problems solved by technology

At present, the synthesis of 2-acyl substituted isoindoline-1-ones is mainly realized by the N-acylation of isoindoline-1-ones. In these methods, the reaction raw material indoline-1-ones needs to be synthesized in advance, Disadvantages such as harsh reaction conditions and use of noble metals (Bioorg.Med.Chem.Lett.2006,16,1151–1155; Can.J.Chem.2005,83,990–1005; Synthesis 2006,8,1333–1338)

Method used

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  • One-step synthesis method of 2-acyl substituted isoindoline-1-one compounds
  • One-step synthesis method of 2-acyl substituted isoindoline-1-one compounds
  • One-step synthesis method of 2-acyl substituted isoindoline-1-one compounds

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0014] Taking the preparation of 4,5,6-trimethoxy-2-benzoylisoindolin-1-one with the following structural formula as an example, the raw materials used and the preparation method are as follows:

[0015]

[0016] Add 0.0212g (0.1mmol) 3,4,5-trimethoxybenzoic acid, 0.0255g (0.2mmol) benzamide, 0.0579g (0.25mmol) 2,3-dichloro-5 ,6-dicyano-p-benzoquinone (DDQ), 0.0360g (0.15mmol) (NH 4 ) 2 S 2 o 8 , 30μL (0.4mmol) DMSO, 0.6mL 1,2-dichloroethane, under the protection of argon in a closed system, stirred and reacted at 130°C for 24 hours, cooled to room temperature after the reaction was completed, filtered through a column chromatography silica gel column, and used Separation by thin-layer chromatography yielded 4,5,6-trimethoxy-2-benzoylisoindolin-1-one with an isolated yield of 68%, and the structural characterization data are as follows:

[0017] 1 H NMR (400MHz, CDCl 3 ): δ(ppm)=7.68(d, J=7.0Hz, 2H), 7.57~7.52(m, 1H), 7.45(t, J=7.5Hz, 2H), 7.09(s, 1H), 4.99(s , 2H), ...

Embodiment 2

[0019] Taking the preparation of 4,5,6-trimethoxy-2-p-tolylisoindolin-1-one with the following structural formula as an example, the raw materials used and the preparation method are as follows:

[0020]

[0021] In Example 1, the benzamide used was replaced with equimolar p-toluamide, and the other steps were the same as in Example 1 to obtain 4,5,6-trimethoxy-2-p-toluylbenzoyl Isoindolin-1-one, its isolated yield is 64%, and the structural characterization data are as follows:

[0022] 1 H NMR (600MHz, CDCl 3 ): δ (ppm) = 7.67 (d, J = 7.9Hz, 2H), 7.34 (d, J = 7.9Hz, 2H), 7.15 (s, 1H), 5.01 (s, 2H), 4.13 (s, 3H ), 4.01(s, 3H), 3.99(s, 3H), 2.48(s, 3H); 13 C NMR (150MHz, acetone-d 6 ): δ (ppm) = 174.6, 171.2, 160.7, 153.7, 151.8, 147.0, 137.6, 134.4, 133.3, 132.1, 131.6, 107.3, 65.6, 65.2, 61.1, 51.4, 25.9; HRMS (ESI) m / z: C 18 h 17 NO 5 , [M+Na] + The theoretical value is 364.1161, and the measured value is 364.1158.

Embodiment 3

[0024] Taking the preparation of 4,5,6-trimethoxy-2-(4-n-butylbenzoyl)isoindolin-1-one with the following structural formula as an example, the raw materials used and the preparation method are as follows:

[0025]

[0026] In Example 1, the benzamide used was replaced with equimolar p-n-butylbenzamide, and the other steps were the same as in Example 1 to obtain 4,5,6-trimethoxy-2-(4-n-butyl Benzoyl) isoindolin-1-one, its isolated yield is 60%, and the structural characterization data are as follows:

[0027] 1 H NMR (400MHz, acetone-d 6): δ (ppm) = 7.63 (d, J = 7.8Hz, 2H), 7.30 (d, J = 7.8Hz, 2H), 7.09 (s, 1H), 4.95 (s, 2H), 4.07 (s, 3H ), 3.94(s, 3H), 3.93(s, 3H), 2.72(t, J=7.7Hz, 2H), 1.70~1.63(m, 2H), 1.43~1.38(m, 2H), 0.95(d, J=7.3Hz, 3H); 13 C NMR (150MHz, acetone-d 6 ): δ (ppm) = 174.7, 171.2, 160.7, 153.7, 151.9, 137.8, 134.4, 134.3, 132.7, 132.1, 131.6, 107.2, 65.6, 65.2, 61.1, 51.4, 40.5, 38.5, 27.3, 18.5; ) m / z: C 22 h 25 NO 5 , [M+Na] + The theoretical...

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Abstract

The invention discloses a one-step synthetic method for 2-acyl substituted isoindoline-1-ketone compounds. The method synthesizes the 2-acyl substituted isoindoline-1-ketone compounds by adopting a one-step process of subjecting aromatic acid with dimethylsulfoxide and amide compounds to tandem cyclization reaction based on C-H functionalization in ortho position of carboxyl. The one-step synthetic method for the 2-acyl substituted isoindoline-1-ketone compounds provided by the invention has the advantages of simple and easily-available raw materials, high efficiency, greenness, etc.

Description

technical field [0001] The present invention relates to a kind of one-step synthesis method of 2-acyl substituted isoindoline-1-one compound, specifically, relates to a kind of 2,3-dichloro-5,6-dicyano-p-benzoquinone and Ammonium persulfate was used as an oxidant to synthesize 2-acyl substituted compounds in a one-step method through the cascade cyclization reaction of 3,4,5-trialkoxybenzoic acid, dimethyl sulfoxide, and amides based on the C—H functionalization of the carboxyl group. Isoindolin-1-ones. Background technique [0002] Cyclic compounds are one of the most diverse and numerous species in organic compounds. Many natural products, pharmaceuticals and synthetic intermediates with important biological activities contain cyclic compound skeletons. For example, the isoindolin-1-one skeleton exists in many natural products (J.Nat.Prod.1982,45,105-122; J.Nat.Prod.1986,49,369; J.Nat.Prod.1981,44,169- 178; Phytochemistry 1994, 36, 519–523; J. Am. Chem. Soc. 1995, 117, ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/46
CPCC07D209/46
Inventor 石先莹王彭敏刘课艳樊娟魏俊发
Owner SHAANXI NORMAL UNIV
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