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A kind of preparation method of substituted 2,3-dihydroquinolone compound

A technology of dihydroquinolones and compounds, which is applied in the field of organic synthesis, can solve the problems of not being widely used, and achieve the effects of strong practicability, wide tolerance and easy operation

Active Publication Date: 2021-09-07
ZHEJIANG SCI-TECH UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, there are few reports on the synthesis of 2,3-dihydroquinolone skeletons based on carbonylation reactions. Relatively speaking, it is not widely used at present, but it has great application potential and needs to be further studied.

Method used

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  • A kind of preparation method of substituted 2,3-dihydroquinolone compound
  • A kind of preparation method of substituted 2,3-dihydroquinolone compound
  • A kind of preparation method of substituted 2,3-dihydroquinolone compound

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Embodiment Construction

[0036] The present invention will be further described below in conjunction with specific embodiments.

[0037] Add bis(acetylacetonate)palladium, 1,3-bis(diphenylphosphine)propane, triethylamine, 1,3,5-mesotricarboxylated phenol ester, N-pyridinesulfonyl-o-iodoaniline (II), olefin (III) and organic solvent 2mL, mixed and stirred evenly, reacted for 48 hours according to the reaction conditions in Table 2, filtered, mixed with silica gel, purified by column chromatography to obtain the corresponding Substituted 2,3-dihydroquinolone compound (I), the reaction process is shown in the following formula:

[0038]

[0039] The raw material addition of table 1 embodiment 1~15

[0040]

[0041]

[0042] Table 2

[0043]

[0044] In Table 1 and Table 2, T is the reaction temperature, t is the reaction time, Ph is phenyl, Me is methyl, OMe is methoxy, t-Bu is tert-butyl, TMS is trimethylsilyl, dioxane For dioxane.

[0045] The structure confirmation data of some compoun...

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Abstract

The invention discloses a preparation method of a substituted 2,3-dihydroquinolone compound, comprising the following steps: adding a palladium catalyst, a ligand, a carbon monoxide substitute, an additive, N-pyridinesulfonyl-o-iodoaniline and an alkene into an organic In a solvent, the reaction is carried out at 100-120° C. for 24-48 hours. After the reaction is complete, post-treatment is performed to obtain the substituted 2,3-dihydroquinolone compound. The preparation method is simple to operate, the starting materials are cheap and easy to obtain, the reaction efficiency is high, and the substrate compatibility is good, and the 2,3-dihydroquinolone compound substituted by the 2-position aryl group and the 3-position alkyl group can also be synthesized through substrate design , which is easy to operate and broadens the practicability of this method.

Description

technical field [0001] The invention belongs to the field of organic synthesis, in particular to a preparation method of a substituted 2,3-dihydroquinolone compound. Background technique [0002] 2,3-Dihydroquinolone compound is an important nitrogen-containing carbonyl-containing six-membered heterocyclic ring, which widely exists in various molecular skeletons with important biological activities. For example, compounds A and B have been confirmed to have significant anticancer activity on human cells (J. Med. Chem. 1998, 41, 1155-1162; J. Med. Chem. 2000, 43, 167-176). Compound C also has potential analgesic activity (J. Med. Chem. 1965, 8, 566-571). [0003] [0004] Due to the extensiveness of the 2,3-dihydroquinolone skeleton, there are now a large number of literatures reporting its synthesis method (Chem. 2019, 5, 1059-1011). The carbonylation reaction provides an important method for the direct and efficient synthesis of carbonyl compounds (Chem. Rev., 2019, 11...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D401/12C07F7/08
CPCC07D401/12C07F7/0812C07F7/083
Inventor 吴小锋应俊汪建树姚凌云
Owner ZHEJIANG SCI-TECH UNIV
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