Preparation method of substituted 2,3-dihydroquinolone compound

A technology for dihydroquinolone and compound, which is applied in the field of organic synthesis, can solve problems such as not being widely used, and achieves the effects of good reaction applicability, strong practicability and convenient post-processing

Active Publication Date: 2021-01-19
ZHEJIANG SCI-TECH UNIV
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  • Summary
  • 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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  • Preparation method of substituted 2,3-dihydroquinolone compound
  • Preparation method of substituted 2,3-dihydroquinolone compound
  • 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, wherein the preparation method comprises the following steps: adding a palladium catalyst, a ligand, a carbon monoxide substitute, an additive, N-pyridylsulfonyl-o-iodobenzidine and olefin into an organic solvent, reacting at the temperature of 100-120 DEG C for 24-48 hours, and after the reaction is completed, carrying out aftertreatment to obtain the substituted 2,3-dihydroquinolone compound. The preparation method is simple to operate, cheap and easily available in initial raw materials, high in reaction efficiency and good in substrate compatibility, the 2-aryl and 3-alkyl substituted 2,3-dihydroquinolone compound can be synthesized through substrate design, the operation is convenient, and thepracticability of the method is broadened.

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 Applications(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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