3-烯丙基喹啉的制备方法

Preparation method of 3-allyl quinoline

Abstract

本发明公开了一种3-烯丙基喹啉的制备方法;该3-烯丙基喹啉结构式为:(I),其中,R1代表连接在苯环上的一个或一个以上的取代基,选自H、卤代物、苯基中的一种,R3为苯基、苯甲基、环己基、苯基卤代物中的一种,R4为烯丙基或乙酰氧基。制备时,以1-叠氮-2-(2-丙炔基)-苯(II)为原料,在Pd(PPh3)4催化剂、碱助催化剂、有机溶剂存在的条件下与甲基碳酸烯丙脂反应,即可。本发明采用高效的一锅法合成3-烯丙基喹啉化合物,转化效率高,反应条件中性,无副产物生成且本方案原料成本低、操作简单、对环境污染小、有利于工业化生产,产物应用广泛,可以作为中间体进一步合成更复杂的化合物。
The invention discloses a preparation method of 3-allyl quinoline. The structural formula of the 3-allyl quinoline is as shown in formula (I), R1 represents one or more substituent groups connected to a benzene ring and selected from H, halide and phenyl; R3 is one selected from phenyl, phenmethyl, cyclohexyl and phenyl halide; and R4 is allyl or acetoxyl group. When in a preparation process, 1-nitrine-2-(2-propinyl)-benzene (II) is used as the raw material to react with a methyl carbonic acid allyl ester in the presence of a Pd(PPh3)4 catalyst, an alkali catalyst promoter and an organic solvent, thus obtaining a product. Through synthesizing 3-allyl quinoline by a high-efficiency one-pot reaction, the conversation efficiency is high, the reaction condition is moderate and no by-product is generated; by adoption of the proposal, the cost of the raw material is low, the operation is simple, the environment pollution is small, and the industrial production is facilitated; and the product is wide in application and can be used as an intermediate for further synthesizing a more complex compound.

Claims

Description

Topics

Download Full PDF Version (Non-Commercial Use)

Patent Citations (2)

    Publication numberPublication dateAssigneeTitle
    CN-101541751-ASeptember 23, 2009惠氏公司Quinoline compounds
    WO-9714681-A1April 24, 1997Fujisawa Pharmaceutical Co., Ltd.Composes heterocycliques tels que des h+-atpases

NO-Patent Citations (2)

    Title
    KEITH JONES,等: "Demethylation of 2,4-dimethoxyquinolines: the synthesis of atanine", 《ORG.BIOMOL.CHEM》, 6 November 2003 (2003-11-06), pages 4380 - 4383
    ZHIBAO HUO: "A Method for the Synthesis of Substituted Quinolines via Electrophilic Cyclization of 1-Azido-2-(2-propynyl)benzene", 《J.ORG.CHEM》, vol. 75, no. 4, 26 January 2010 (2010-01-26), pages 1266 - 1270

Cited By (2)

    Publication numberPublication dateAssigneeTitle
    CN-104478799-AApril 01, 2015上海交通大学1,4-二烯丙基异喹啉的制备方法
    CN-104478799-BNovember 16, 2016上海交通大学1,4-二烯丙基异喹啉的制备方法