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Method for preparing isoquinoline dione from methoxybenzamide and diazotate ester through carbon-hydrogen functionalization

A technology of methoxybenzamide and diazomalonate is applied in the directions of organic chemistry, drug combination, antitumor drugs, etc., and can solve the problems of consumption of raw materials and energy, low total reaction yield, energy waste and the like, Achieve the effect of avoiding the use of oxidants, reducing costs and reducing pollution

Inactive Publication Date: 2017-10-24
ZHEJIANG UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] Journal of Heterocycle Chemistry, 46,392-398,2009 informed method is: take 2-carboxymethylphenylacetic acid as the multi-step reaction (formula 1) of raw material to prepare 4-ester group-isoquinoline-1,3- Diketone compounds; this method requires more expensive raw materials, multi-step and complicated reactions, very low overall reaction yield, consumes a large amount of raw materials and energy, and causes energy waste

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  • Method for preparing isoquinoline dione from methoxybenzamide and diazotate ester through carbon-hydrogen functionalization
  • Method for preparing isoquinoline dione from methoxybenzamide and diazotate ester through carbon-hydrogen functionalization
  • Method for preparing isoquinoline dione from methoxybenzamide and diazotate ester through carbon-hydrogen functionalization

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Embodiment 1

[0042] Add N-methoxybenzamide (0.10mmol) into a 20mL test tube with a stirring bar, and add [RhCp*Cl 2 ] 2(1.2mg, 0.002mmol, 2.0mol%), AgSbF 6 (3.5mg, 0.01mol, 10mol%), AcOH (12mg, 0.20mmol), diethyl 2-diazomalonate (0.25mmol) and solvent ethanol (2.0mL), nitrogen protection, and then insert a nitrogen balloon The test tube was placed in an oil bath at 100°C for 12 hours. After the reaction is finished, cool to room temperature, and the mixed solution is concentrated and evaporated to dryness with a rotary evaporator under reduced pressure. The residue is purified by column chromatography (using a built-in 200-300 mesh silica gel as a chromatographic column), and the eluent is petroleum ether / ethyl acetate Ester = 20 / 1 (v / v) to 5 / 1 (v / v), resulting in 4-esteryl-isoquinoline-1,3-dione compound 3a.

[0043] The raw materials used for compounds 3b-3n are described in Table 1 below, and the details of the eluent used for purification are as follows; the rest are the same as in ...

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Abstract

The invention discloses a method for preparing isoquinoline dione from methoxybenzamide and diazotate ester through carbon-hydrogen functionalization, which comprises the following steps: (1) reacting in a solvent under protection of an inert gas at 100+ / -5DEG C for 12+ / -1 hours by using substituted N-methoxybenzamide and diazo-malonate as substrates, [RhCp*Cl2]2 / AgSbF6 as a catalyst and acetic acid as an additive; and (2) cooling the reaction product obtained in the step (1) to room temperature, concentrating, performing column chromatographic purification on residues with a mixed liquid which is the column chromatographic purification eluting liquid and has a volume ratio of petroleum ether to ethyl acetate being (30-1):1 to obtain 4-ester-isoquinoline-1,3-diketone compound.

Description

technical field [0001] The present invention relates to the method for the preparation of isoquinolinediones through carbon-hydrogen functionalization of methoxybenzamide and diazonium ester, that is, involves the carbon-hydrogen functionalization of N-methoxybenzamide and diazomalonate Method for the preparation of 4-esteryl-isoquinoline-1,3-diones by hydrogen functionalization. Background technique [0002] 4-Substituted-isoquinoline-1,3-dione structural units widely exist in natural products and drug molecules, and many molecules containing 4-substituted-isoquinoline-1,3-dione structures have important physiological activities , can be used as an HIV-1 integrase inhibitor (ACS Medicinal Chemistry Letters, 4,606,2013), an active agent against human pancreatic cancer cells (Journal of Medicinal Chemistry, 54,1812,2011) and a cyclin-dependent kinase inhibitor (Journal of Medicinal Chemistry, 51, 3507, 2008) etc. Therefore, exploring new synthetic methods of 4-substituted-i...

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D217/26A61P35/00
CPCC07D217/26
Inventor 白鹏肯尼思 L.黄黄志真
Owner ZHEJIANG UNIV