The use of enaminones and enamines as effective synthons for MSA-catalyzed regioselective synthesis of 1,3,4-tri- and 1,3,4,5-tetrasubstituted pyrazoles

被引：14

作者：

Duan, Liancheng ^{[1
,2
]}

Zhou, Hui ^{[1
,2
]}

Gu, Yucheng ^{[1
,2
]}

Gong, Ping ^{[1
,2
]}

Qin, Mingze ^{[1
,2
]}

机构：

[1] Shenyang Pharmaceut Univ, Key Lab Struct Based Drug Design & Discovery, Minist Educ, 103 Wenhua Rd, Shenyang 110016, Liaoning, Peoples R China

[2] Syngenta Jealotts Hill Int Res Ctr, Bracknell RG42 6EY, Berks, England

来源：

NEW JOURNAL OF CHEMISTRY | 2019年 / 43卷 / 41期

关键词：

DNA GYRASE INHIBITORS; ANTIBACTERIAL ACTIVITY; KETONES; LIGANDS; DERIVATIVES; HYDRAZONES; AMINATION;

D O I：

10.1039/c9nj03701b

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

In the present work, an efficient regioselective synthesis of 1,3,4-tri- and 1,3,4,5-tetrasubstituted pyrazoles via a methanesulfonic acid (MSA)-catalyzed reaction of hydrazones with enaminones or enamines is reported. Mechanistically, the formation of the title compounds involves the [2+3] cycloaddition of hydrazones with enaminones or enamines followed by aromatization with acid and oxygen. This convenient method under mild conditions with various hydrazones, enaminones, and enamines was well-tolerated to afford products in good to excellent yields. Compared with the literature methods, this strategy has advantages such as materials that are available economically, metal-free catalysis, excellent regioselectivity, and high efficiency.

引用

页码：16131 / 16137

页数：7