Preparation method of 3-alkenyl quinoline-2 (1H) ketone derivative

An alkenylquinoline and derivative technology, which is applied in the field of preparation of 3-alkenylquinoline-2 ketone derivatives, can solve problems such as limited research on carbonylation reaction, and achieves simple preparation method, wide tolerance range and easy operation. Effect

Active Publication Date: 2022-05-13
ZHEJIANG SCI-TECH UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, studies on the carbonylation reactions involving such compounds are still very limited, and most carbonylation reactions mainly use allyl chloride, acetate, carbonate, and phosphate as electrophiles

Method used

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  • Preparation method of 3-alkenyl quinoline-2 (1H) ketone derivative
  • Preparation method of 3-alkenyl quinoline-2 (1H) ketone derivative
  • Preparation method of 3-alkenyl quinoline-2 (1H) ketone derivative

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Embodiment 1～15

[0033] Add palladium acetate, tris(3-methoxyphenyl)phosphine, molybdenum carbonyl, cesium carbonate, tetrabutylammonium iodide, o-nitrobenzaldehyde (II) into a 15mL sealed tube according to the raw material ratio in Table 1 and allyl aryl ether (III), then add acetonitrile (1mL), mix and stir evenly, react according to the reaction conditions in Table 2, after the reaction is completed, filter, sample with silica gel, and obtain the corresponding 3- Alkenyl quinoline-2 (1H) ketone derivatives (I), the reaction process is shown in the following formula:

[0034]

[0035] The raw material addition of table 1 embodiment 1~15

[0036]

[0037] Table 2

[0038]

[0039]

[0040] In Table 1 and Table 2, T is the reaction temperature, t is the reaction time, Me is methyl, Pr is propyl, t-Bu is methyl, OMe is methoxy, CF 3 For trifluoromethyl.

[0041] The structural confirmation data of the compounds prepared in Examples 1-5:

[0042] The nuclear magnetic resonance of...

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Abstract

The invention discloses a preparation method of a 3-alkenyl quinoline-2 (1H) ketone derivative, which comprises the following steps: carrying out reaction on palladium acetate, tris (3-methoxyphenyl) phosphine, carbonyl molybdenum, cesium carbonate, tetrabutylammonium iodide, o-nitrobenzaldehyde and allyl aryl ether at 100 DEG C for 30 hours, and after the reaction is completed, carrying out post-treatment to obtain the 3-alkenyl quinoline-2 (1H) ketone derivative. According to the preparation method, o-nitrobenzaldehyde is used as a nitrogen source and a formyl source, the operation is simple, the reaction initial raw materials are cheap and easy to obtain, the tolerance range of substrate functional groups is wide, and the reaction efficiency is high. Various 3-alkenyl quinoline-2 (1H) ketone derivatives can be synthesized according to actual needs, and the practicability of the method is widened while the operation is convenient.

Description

technical field [0001] The invention belongs to the field of organic synthesis, in particular to a preparation method of 3-alkenyl quinolin-2 (1H) ketone derivatives. Background technique [0002] Nitrogen-containing heterocyclic compounds widely exist in various natural products and biologically active compounds, especially quinolin-2(1H)-one and its derivatives, as special building blocks, exhibit a variety of pharmaceutical activities and are often Used as antibiotics, antineoplastic drugs, antiplatelet drugs, endothelin receptor antagonists and angiotensin II receptor antagonists (J.Med.Chem.1997,40,754-765). Some quinolin-2(1H)-ones, such as nybomycin and deoxynybomyin, have become effective antibacterial agents. In addition, quinolin-2(1H)one derivatives can also be used as intermediates in organic synthesis and play a very important role (J. Am. Chem. Soc. 2002, 124, 7982-7990). Therefore, the synthesis of quinolin-2(1H)one derivatives has attracted widespread atten...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D215/227C07D405/06
CPCC07D215/227C07D405/06Y02A50/30
Inventor 祁昕欣刘建利王尉吴小锋
Owner ZHEJIANG SCI-TECH UNIV
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