Title:
SIMPLE PREPARATION METHOD FOR ISOXAZOLINES
Document Type and Number:
WIPO Patent Application WO/2022/206010
Kind Code:
A1
Abstract:
Disclosed in the present invention is a simple preparation method for isoxazolines, comprising: using aldehyde, p-toluenesulfonyl hydrazide, olefin, and tert-butyl nitrite as a substrate, using copper chloride as a catalyst, using tetramethylethylenediamine (TMEDA) as an alkali, and efficiently synthesizing a series of isoxazoline compounds buy using a one-pot two-step method. The advantages are as follows: the catalyst is cheap, the reaction is economical, substrate universality is wider, raw materials are easy to obtain, later stage functionalization is more convenient, reaction conditions are mild, and the gram-scale reaction is good; and in particular, in the present invention, a product can be obtained at a moderate yield in the absence of catalyst, post-treatment is simple and convenient, and it is beneficial to an application in drug molecule synthesis and large-scale industrialization, thereby satisfying the requirements and directions of contemporary green chemistry and pharmaceutical chemistry.
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Inventors:
WAN XIAOBING (CN)
MA LIANG (CN)
CHENG XIONGLUE (CN)
JIANG GANGZHONG (CN)
TAO SUYAN (CN)
LI XINGXING (CN)
YANG JINWEI (CN)
MA LIANG (CN)
CHENG XIONGLUE (CN)
JIANG GANGZHONG (CN)
TAO SUYAN (CN)
LI XINGXING (CN)
YANG JINWEI (CN)
Application Number:
PCT/CN2021/136208
Publication Date:
October 06, 2022
Filing Date:
December 07, 2021
Export Citation:
Assignee:
UNIV SOOCHOW (CN)
International Classes:
C07D261/04; C07D413/04; C07D417/04
Foreign References:
| CN113149924A | 2021-07-23 | |||
| CN107118171A | 2017-09-01 | |||
| CN105198824A | 2015-12-30 | |||
| CN107721941A | 2018-02-23 | |||
| CN104039149A | 2014-09-10 | |||
| US20110144334A1 | 2011-06-16 | |||
| JP2008239611A | 2008-10-09 | |||
| CN103588720A | 2014-02-19 |
Other References:
MA LIANG, JIN FENG, CHENG XIONGLVE, TAO SUYAN, JIANG GANGZHONG, LI XINGXING, YANG JINWEI, BAO XIAOGUANG, WAN XIAOBING: "[2 + 2 + 1] Cycloaddition of N -tosylhydrazones, tert -butyl nitrite and alkenes: a general and practical access to isoxazolines", CHEMICAL SCIENCE, ROYAL SOCIETY OF CHEMISTRY, UNITED KINGDOM, vol. 12, no. 28, 21 July 2021 (2021-07-21), United Kingdom , pages 9823 - 9830, XP055972131, ISSN: 2041-6520, DOI: 10.1039/D1SC02352G
DATABASE REGISTRY 16 November 1984 (1984-11-16), ANONYMOUS : "-Isoxazole, 3-(4-bromophenyl)-4,5-dihydro-5-phenyl- (CA INDEX NAME) ", XP055972135, retrieved from STN Database accession no. 20822-01-9
WANG DANJUN, BEI-YI CHEN,YI-QI WANG,XIAO-WEI ZHANG: "Ruthenium-Catalyzed Direct Transformation of Alkenyl Oximes to 5-Cyanated Isoxazolines: A Cascade Approach Based on Non-Stabilized Radical Intermediate", EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, vol. 2018, no. 11, 31 January 2018 (2018-01-31), pages 1342 - 1346, XP055972134, ISSN: 1099-0690, DOI: 10.1002/ejoc.201701651
DATABASE REGISTRY 16 November 1984 (1984-11-16), ANONYMOUS : "-Isoxazole, 3-(4-bromophenyl)-4,5-dihydro-5-phenyl- (CA INDEX NAME) ", XP055972135, retrieved from STN Database accession no. 20822-01-9
WANG DANJUN, BEI-YI CHEN,YI-QI WANG,XIAO-WEI ZHANG: "Ruthenium-Catalyzed Direct Transformation of Alkenyl Oximes to 5-Cyanated Isoxazolines: A Cascade Approach Based on Non-Stabilized Radical Intermediate", EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, vol. 2018, no. 11, 31 January 2018 (2018-01-31), pages 1342 - 1346, XP055972134, ISSN: 1099-0690, DOI: 10.1002/ejoc.201701651
Attorney, Agent or Firm:
SUZHOU CREATOR PATENT AND TRADEMARK AGENCY, LTD (CN)
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